Supporting Information (DFT Calculations) Pd-Catalyzed C-H Functionalization of Acyldiazomethane. and Tandem Cross-Coupling Reactions
|
|
|
- Heather Sherman
- 5 years ago
- Views:
Transcription
1 Supporting Information (DFT Calculations) Pd-Catalyzed C-H Functionalization of Acyldiazomethane and Tandem Cross-Coupling Reactions Fei Ye,, Shuanglin Qu,, Lei Zhou,, Cheng Peng, Chengpeng Wang, Jiajia Cheng, Mohammad Lokman Hossain, Yizhou Liu, Yan Zhang, Zhi-Xiang Wang,*, and Jianbo Wang*, Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing , China School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing , China School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou , China CONTENTS 1) Computational details..... S2 2) Additional computational results not shown in the main text... S3 3) Results for the alternative pathway leading K to 6a and catalyst A - via the HCO 3 moiety offering a hydrogen atom S5 4) Molecular orbital analysis... S7 5) Energies and Cartesian coordinates of all structures... S8 6) References S35 S1
2 1) Computational details All the structures were optimized and characterized to be energy minima or transition states at M06 1 /BSI level, where BSI denotes a basis set of LANL2DZ 2 for Pd, I, Ag and 6-31G(d) 3 for other atoms. The energies were then improved by M06/BSII//M06/BSI single point calculations with the solvent effects accounted by SMD 4 solvent model, using toluene as the solvent,where BSII denotes a basis set of SDD 5 for Pd, I, Ag and G(d,p) 3,6 for other atoms. Wiberg bond indices (bond order) were calculated at the B3LYP/BSI level according to the natural orbital (NBO) method. 7 The thermal corrections to free energies were carried out at K and 1atm, using M06/BSI harmonic frequencies. It should be emphasized that such thermal corrections based on the ideal gas phase model inevitably overestimate entropy contributions to free energies for reactions in solvent, in particular for reactions involving multi-component change, because of ignoring the suppressing effect of solvent on the rotational and transitional freedoms of substrates. The entropy overestimation by ideal gas phase model was also demonstrated by experimental studies. 8,9 Since no standard quantum mechanics-based approach is available to accurately calculate entropy in solution, we adopted the approximate approach proposed by Martin et al. 10 According to their approach, a correction of 4.3 kcal/mol applies to per component change for a reaction at K and 1atm (i.e., a reaction from m- to n-components has an additional correction of (n-m) 4.3 kcal/mol). Previously, we applied the correction protocol for mechanistic studies of various catalytic reactions and found such corrected free energies were more reasonable than enthalpies and uncorrected free energies, 11 although the protocol is by no means accurate. We discuss the mechanism in terms of the corrected free energies and give the enthalpies for references in the brackets in the relevant figures. All the calculations were performed using GAUSSIAN 09 program. S2
3 2) Additional computational results not shown in the main text Figure S1. Energy profile of Coupling I with the AgI moiety reserved. Figure S2. Energy profile of dediazoniation and migratory insertion in Coupling II with the AgI moiety reserved. S3
4 Figure S3. Energy profile of deprotonation by NEt 3. Figure S4. Energy profiles of dediazoniation without the involvement of AgHCO 3. S4
5 3) Results for the alternative pathway leading K to 6a and catalyst A via the HCO - 3 moiety offering a hydrogen atom - We examined two possibilities to complete the transformation. First, the HCO 3 moiety in K transfers the H atom to -C(Ph) 2 COOEt fragment directly (Figure S5). The barrier (35.1 kcal/mol, TS8 relative to K) is 6.0 kcal/mol higher than the barrier for the mechanism illustrated in Figure 3 in the main text. Second, the HCO - 3 moiety in K transfers the H atom to the Pd(II) center, then the H atom moved to -C(Ph) 2 COOEt fragment. Under this consideration, as shown in Figure S6, the HCO - 3 moiety first isomerizes to allow the H atom getting close to the Pd center, leading to a less stable R (by 4.4 kcal/mol). Attempts to locate a transition state for transferring the hydrogen of HCO - 3 moiety to the Pd center were failed. However, the hydrogen transfer would lead to a Pd(IV) complex (S) which is 52.6 kcal/mol higher than K, indicating that the this pathway is inaccessible. Thus it could be safe to conclude that the alternative pathway is unlikely. Figure S5. Energy profile of the hydrogen transfer from the HCO3 - to the -C(Ph) 2 COOEt fragment. S5
6 Figure S6. (a) Energy profile of the hydrogen transfer from the HCO3 - to the Pd(II) center, leading to a Pd(IV) complex S. (b) Key optimized structures with selected bond lengths in angstroms. Trivial hydrogen atoms are omitted for clarity. S6
7 4) Molecular orbital analysis Figure S7. Comparison of the and molecular orbitals involved in the formal Pd=C double bonds in complex J and Pd-carbene. Trivial hydrogen atoms are omitted for clarity. S7
8 5) Energies and Cartesian coordinates of structures The followings are SCF energies (in au), solvated free energies (in au) and Cartesian coordinates for all optimized structures. A (Pd(PPh 3 ) 2 ) SCF energy: Enthalpy in toluene: Free energy in toluene: Pd P P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H PhI SCF energy: Enthalpy in toluene: Free energy in toluene: C C C C C C H H H H H I B SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C C C H H H H H P C C C C H C H C H H H C C S8
9 C C H C H C H H H C C C C H C H C H H H P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H I Ag 2 CO 3 SCF energy: Enthalpy in toluene: Free energy in toluene: C O O O Ag Ag PPh 3 SCF energy: Enthalpy in toluene: Free energy in toluene: P C C C C C C C C C C C C H H H C C C H H H C C C H H H H H H H H H C SCF energy: Enthalpy in toluene: Free energy in toluene: Pd P C C C C H C H C H H H I C C C C H C H C H H H S9
10 C C C C H C H C H H H C C C C H C H C H H H C O O O Ag Ag AgI SCF energy: Enthalpy in toluene: Free energy in toluene: I Ag (AgI) 2 SCF energy: Enthalpy in toluene: Free energy in toluene: I Ag I Ag D SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C O O O Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H a (EDA) SCF energy: Enthalpy in toluene: Free energy in toluene: C H C O O C H H C H H H N N E SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H S10
11 C H H H C H C O O C H H C H H H N N C O O O Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H TS1 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C H C O O C H H C H H H N N C O O O Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H TS2 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C S11
12 C H C H C H H H C H C O O C H H C H H H N N P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C O O O Ag F SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C H C O O C H H C H H H N N C O O O Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H TS3 SCF energy: S12
13 Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C C O O C H H C H H H N N P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H H C O O O Ag a SCF energy: Enthalpy in toluene: Free energy in toluene: C C C C H C H C H H H C C O O C H H C H H H N N AgHCO 3 SCF energy: Enthalpy in toluene: Free energy in toluene: H C O O O Ag E SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H I C H C O O C H H C S13
14 H H H N N C O O O Ag Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H TS1 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H I C H C O O C H H C H H H N N C O O O Ag Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H TS2 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H I C S14
15 H C O O C H H C H H H N N C O O O Ag Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H F SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H I C H C O O C H H C H H H N N C O O O Ag Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H TS3 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C S15
16 C C C H C H C H H H I C H C O O C H H C H H H N N C O O O Ag Ag P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H AgI AgHCO 3 SCF energy: Enthalpy in toluene: Free energy in toluene: I H C O O O Ag Ag G SCF energy: Enthalpy in toluene: Free energy in toluene: Pd P C C C C H C H C H H H I C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C O O O S16
17 Ag H H SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C O O O P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H H I SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C C O O C H H C H H H N N P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C O O S17
18 O H TS4 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C C O O C H H C H H H N N P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C O O O H N 2 SCF energy: Enthalpy in toluene: Free energy in toluene: N N J SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C C O O C H H C H H H P C C C C H C H C H H H C C C C H C S18
19 H C H H H C C C C H C H C H H H C C C C H C H C H H H C O O O H TS5 SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C C O O C H H C H H H P C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C C C C H C H C H H H C O O O H K SCF energy: Enthalpy in toluene: Free energy in toluene: Pd C C C C H C H C H H H C C O O C H H C H S19
Palladium(0)-Catalyzed C(sp 3 )-Si Bond Formation via Formal Carbene Insertion into Si-H Bond
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information (ESI) Palladium(0)-Catalyzed C(sp 3 )-Si Bond Formation via
Supporting Information for
Supporting Information for Factors Controlling the Reactivity and Chemoselectivity of Resonance Destabilized Amides in Ni-catalyzed Decarbonylative and Non-decarbonylative Suzuki-Miyaura Coupling Chong-Lei
Supporting Information
Supporting Information Formation of Ruthenium Carbenes by gem-hydrogen Transfer to Internal Alkynes: Implications for Alkyne trans-hydrogenation Markus Leutzsch, Larry M. Wolf, Puneet Gupta, Michael Fuchs,
Supporting Information
Supporting Information Z-Selective Ethenolysis With a Ruthenium Metathesis Catalyst: Experiment and Theory Hiroshi Miyazaki,, Myles B. Herbert,, Peng Liu, Xiaofei Dong, Xiufang Xu,,# Benjamin K. Keitz,
Jeff Turner Dr Scanlon Dr. Scanlon Ripon College
Jeff Turner Dr Scanlon Dr. Scanlon Ripon College Importance of Nitrene Insertion Carbon Nitrogen bonds are useful in a chemical synthesis. Biomolecules Pharmaceuticals i l Specialized materials Formation
Supporting Information for. Unveiling the Role of Base and Additive in the Ullmann-type of Arene-Aryl C- C Coupling Reaction
S1 Supporting Information for Unveiling the Role of Base and Additive in the Ullmann-type of Arene-Aryl C- C Coupling Reaction Manjaly J. Ajitha, a Fathima Pary, b Toby L. Nelson b, *, and Djamaladdin
Supporting Information
S1 Supporting Information A Radical Mechanism of Isocyanide-Alkyne Cycloaddition by Multi-catalysis of Ag 2 CO 3, Solvent, and Substrate Pin Xiao, Haiyan Yuan, Jianquan Liu, Yiying Zheng, Xihe Bi,* and
Supporting Information. Silylated Organometals: A Family of Recyclable. Homogeneous Catalysts
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 14 Supporting Information lylated rganometals: A Family of Recyclable Homogeneous Catalysts Jian-Lin
Towards a Molecular Understanding of Energetics in Li-S Batteries using Non-Aqueous Electrolytes: A High-level Quantum Chemical Study
Supporting Information Towards a Molecular Understanding of Energetics in Li-S Batteries using Non-Aqueous Electrolytes: A High-level Quantum Chemical Study Rajeev S. Assary a,b*, Larry A. Curtiss a,b,*,
Thiourea Derivatives as Brønsted Acid Organocatalysts
Supporting Information Thiourea Derivatives as Brønsted Acid Organocatalysts Ádám Madarász, Zsolt Dósa, Szilárd Varga, * Tibor Soós, Antal Csámpai, Imre Pápai * Institute of Organic Chemistry, Research
Supporting Information Computational Part
Supporting Information Computational Part Ruthenium-Catalyzed Alkyne trans-hydrometalation: Mechanistic Insights and Preparative Implications Dragoş Adrian Roşca, Karin Radkowski, Larry M. Wolf, Minal
Angucycline Glycosides from Mangrove-Derived Streptomyces diastaticus subsp. SCSIO GJ056
Supporting Information Angucycline Glycosides from Mangrove-Derived Streptomyces diastaticus subsp. SCSIO GJ056 Chun Gui 1,2, Yena Liu 3, Zhenbin Zhou 1,2, Shanwen Zhang 1,2, Yunfeng Hu 1, Yu-Cheng Gu
Investigation of the Role and Form. Formation. Michael Enright
Investigation of the Role and Form of Silver Catalysts in C N Bond Formation Michael Enright Ripon College Importance Carbon Nitrogen Bonds Medicine Biological compounds Make C N bonds whenever we want
Electronic Supplementary Information. for
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information for Two Chiral Catalysts in Action: Insights on Cooperativity
A Dihydride Mechanism Can Explain the. Intriguing Substrate Selectivity of Iron-PNP-
SUPPORTING INFORMATION A Dihydride Mechanism Can Explain the Intriguing Substrate Selectivity of Iron-PNP- Mediated Hydrogenation Glenn R. Morello, Kathrin H. Hopmann* Centre for Theoretical and Computational
Layered SiC Sheets: A Potential Catalyst for Oxygen Reduction Reaction. Materials Science and Engineering, Jilin University, Changchun , China,
Supporting Information Layered SiC Sheets: A Potential Catalyst for Oxygen Reduction Reaction P. Zhang 1,2, B. B. Xiao 1, X. L. Hou 1,2, Y. F. Zhu 1,* Q. Jiang 1 1 Key Laboratory of Automobile Materials,
Trace Solvent as a Predominant Factor to Tune Dipeptide. Self-Assembly
Trace Solvent as a Predominant Factor to Tune Dipeptide Self-Assembly Juan Wang,, Kai Liu,,, Linyin Yan,, Anhe Wang, Shuo Bai, and Xuehai Yan *,, National Key Laboratory of Biochemical Engineering, Institute
Fullerene peroxides in cage-opening reactions*
Pure Appl. Chem., Vol. 78, No. 4, pp. 841 845, 2006. doi:10.1351/pac200678040841 2006 IUPAC Fullerene peroxides in cage-opening reactions* Liangbing Gan Key Laboratory of Bioorganic Chemistry and Molecular
Theoretical study of the BF 3-promoted rearrangement of oxiranyl N-methyliminodiacetic acid boronates
Theoretical study of the BF 3-promoted rearrangement of oxiranyl N-methyliminodiacetic acid boronates Margarita M. Vallejos a* and Silvina C. Pellegrinet b* a Laboratorio de Química Orgánica, IQUIBA-NEA,
Supplementary Figure S1 Stable structures of I, I', II, and II' optimized at the
H C Si 2.492 (2.348) 1.867 (2.005) Fe O 2.106 (2.077) 2.360 (2.497) N 1.126 (1.115) 2.105 (2.175) I quintet (triplet) 0.0 (+4.1) kcal/mol II triplet (quintet) 0.0 (+4.3) kcal/mol 1.857 (2.076) 2.536 (2.351)
Supporting Information
Quantum Chemistry Study of U(VI), Np(V) and Pu(IV,VI) Complexes with Preorganized Tetradentate Phenanthroline Amide Ligands Cheng-Liang Xiao, Qun-Yan Wu, Cong-Zhi Wang, Yu-Liang Zhao, Zhi-Fang Chai, *
Chemistry 4021/8021 Computational Chemistry 3/4 Credits Spring Semester 2013 Answer Key
Chemistry 4021/8021 Computational Chemistry 3/4 Credits Spring Semester 2013 Answer Key 1. Let's return to our favorite natural products from the first problem set. In the templates subdirectory of my
Homework Problem Set 5 Solutions. E e + H corr (a.u.) a.) Determine the bond dissociation enthalpy of ethane in kcal/mol (1 a.u. = kcal/mol).
Chemistry 380.37 Dr. Jean M. Standard Homework Problem Set 5 Solutions 1. Given below are the sum of electronic and thermal enthalpies, E e + H corr, from Hartree-Fock calculations using a 6-31G(d) basis
Supporting Information. Computational Exploration of Concerted and Zwitterionic. Mechanisms of Diels Alder Reactions between 1,2,3-Triazines and
Supporting Information Computational Exploration of Concerted and Zwitterionic Mechanisms of Diels Alder Reactions between 1,2,3-Triazines and Enamines and Acceleration by Hydrogen-Bonding Solvents Yun-Fang
New Bisphosphomide Ligands, 1,3-Phenylenebis((diphenylphosphino)methanone) [1,3-
New Bisphosphomide Ligands, 1,3-Phenylenebis((diphenylphosphino)methanone) [1,3- Ph 2 PC(O)} 2 C 6 H 4 ] and (2-Bromo-1,3-phenylene)bis((diphenylphosphino)methanone) [1,3- Ph 2 PC(O)} 2 C 6 H 4 Br]: Synthesis,
Supporting Information
Supporting Information Hydrogen-bonding Interactions Between [BMIM][BF 4 ] and Acetonitrile Yan-Zhen Zheng, a Nan-Nan Wang, a,b Jun-Jie Luo, a Yu Zhou a and Zhi-Wu Yu*,a a Key Laboratory of Bioorganic
How Partial Atomic Charges and Bonding. Orbitals Affect the Reactivity of Aluminum
Supporting Information for: How Partial Atomic Charges and Bonding Orbitals Affect the Reactivity of Aluminum Clusters with Water? Anthony M.S Pembere ξ, Xianhu Liu ξ, Weihua Ding, Zhixun Luo * State Key
NH 3 inversion: Potential energy surfaces and transition states CH342L March 28, 2016
N 3 inversion: Potential energy surfaces and transition states C342L March 28, 2016 Last week, we used the IR spectrum of ammonia to determine the splitting of energy levels due to inversion of the umbrella
SUPPORTING INFORMATION. Ammonia-Borane Dehydrogenation Promoted by a Pincer-Square- Planar Rhodium(I)-Monohydride: A Stepwise Hydrogen Transfer
S 1 SUPPORTING INFORMATION Ammonia-Borane Dehydrogenation Promoted by a Pincer-Square- Planar Rhodium(I)-Monohydride: A Stepwise Hydrogen Transfer from the Substrate to the Catalyst Miguel A. Esteruelas,*
Unraveling Surface Plasmon Decay in Core Shell Nanostructures towards Broadband Light-Driven Catalytic Organic Synthesis
Supporting Information Unraveling Surface Plasmon Decay in Core Shell Nanostructures towards Broadband Light-Driven Catalytic Organic Synthesis Hao Huang,, Lei Zhang,, Zhiheng Lv, Ran Long, Chao Zhang,
Mechanism of Hydrogen Evolution in Cu(bztpen)-Catalysed Water Reduction: A DFT Study
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Supporting Information to Mechanism of Hydrogen Evolution in Cu(bztpen)-Catalysed Water
Titanium Phosphinimide Polymerization Catalysts
tanium Phosphinimide Polymerization atalysts Motivation We are all familiar with the importance of Ziegler-atta catalysis [l 4 and cocatalyst Et 3 Al], and the polymerisation of olefins which represents
Organic Chemistry Laboratory Summer Lecture 6 Transition metal organometallic chemistry and catalysis July
344 Organic Chemistry Laboratory Summer 2013 Lecture 6 Transition metal organometallic chemistry and catalysis July 30 2013 Summary of Grignard lecture Organometallic chemistry - the chemistry of compounds
Cethrene: The Chameleon of Woodward Hoffmann Rules
Supporting Information Cethrene: The Chameleon of Woodward Hoffmann Rules Tomáš Šolomek,*, Prince Ravat,, Zhongyu Mou, Miklos Kertesz, and Michal Juríček*,, Department of Chemistry, University of Basel,
Supporting Information
Supporting Information Synthesis of Robust MOF-derived Cu/SiO 2 Catalyst with Low Copper Loading via Sol-gel Method for the Dimethyl Oxalate Hydrogenation Reaction Run-Ping Ye,,, # Ling Lin, # Chong-Chong
Synthesis of Polyynes Using Dicobalt Masking Groups
Supporting Information Synthesis of Polyynes Using Dicobalt Masking Groups Daniel R. Kohn, Przemyslaw Gawel, Yaoyao Xiong, Kirsten E. Christensen, and Harry L. Anderson* University of Oxford, Department
Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: Competing routes to C C bond formation
Supporting Information Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: Competing routes to C C bond formation Andrea Hamza, a Gábor Schubert, a Tibor Soós b and Imre
Selected Publications of Prof. Dr. Wenjian Liu
Selected Publications of Prof. Dr. Wenjian Liu College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China 1 Fundamentals of relativistic molecular quantum mechanics 1. Handbook
The Mechanism of Directed Ni(II)-Catalyzed C H Iodination with Molecular Iodine
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2017 Supporting Information The Mechanism of Directed Ni(II)-Catalyzed C H Iodination with Molecular
A mechanistic study supports a two-step mechanism for peptide bond formation on the ribosome
s1 Electronic Supplementary Information A mechanistic study supports a two-step mechanism for peptide bond formation on the ribosome Byung Jin Byun and Young Kee Kang* Department of Chemistry, Chungbuk
Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical
![Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical](/thumbs/83/88734510.jpg "Supporting Information. For. Organic Semiconducting Materials from Sulfur-Hetero. Benzo[k]fluoranthene Derivatives: Synthesis, Photophysical")
upporting Information For Organic emiconducting Materials from ulfur-hetero Benzo[k]fluoranthene Derivatives: ynthesis, Photophysical Properties and Thin Film Transistor Fabrication Qifan Yan, Yan Zhou,
C(sp)-C(sp 3 ) Bond Formation through Cu-Catalyzed Cross-Coupling of N-Tosylhydrazones and Trialkylsilylethyne
Supporting Information for C(sp)-C(sp 3 ) Bond Formation through Cu-Catalyzed Cross-Coupling of N-Tosylhydrazones and Trialkylsilylethyne Fei Ye, Xiaoshen Ma, Qing Xiao, Huan Li, Yan Zhang, Jianbo Wang*,,
Supporting Information. Mechanistic Insight to Selective Catalytic Reduction. A DFT Study
Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 05 Supporting Information Mechanistic Insight to Selective Catalytic Reduction
A systematic theoretical study on FeO x -supported single-atom catalysts: M 1 /FeO x for CO oxidation
Electronic Supplementary Material A systematic theoretical study on FeO x -supported single-atom catalysts: M 1 /FeO x for CO oxidation Jinxia Liang 1,2,3, Qi Yu 2, Xiaofeng Yang 4 ( ), Tao Zhang 4, and
Reaction chemistry of complexes Three general forms: 1. Reactions involving the gain and loss of ligands a. Ligand Dissoc. and Assoc. (Bala) b.
eaction chemistry of complexes Three general forms: 1. eactions involving the gain and loss of ligands a. Ligand Dissoc. and Assoc. (Bala) b. Oxidative Addition c. eductive Elimination d. Nucleophillic
Supporting Information
Supporting Information Indirect Four-Electron Oxygen Reduction Reaction on Carbon Materials Catalysts in Acidic Solutions Guo-Liang Chai* 1, Mauro Boero 2, Zhufeng Hou 3, Kiyoyuki Terakura 3,4 and Wendan
Supplementary Information for: Hydrogen abstraction by photoexcited benzophenone: consequences for DNA photosensitization
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2016 Supplementary Information for: Hydrogen abstraction by photoexcited benzophenone:
Supporting Information. DFT Study on the Homogeneous Palladium-Catalyzed. N-Alkylation of Amines with Alcohols
Supporting Information DFT Study on the Homogeneous Palladium-Catalyzed N-Alkylation of Amines with Alcohols Guo-Ming Zhao,, Hui-ling Liu, *, Xu-ri Huang, Xue Yang, and Yu-peng Xie Institute of Theoretical
Mechanisms of H- and OH-assisted CO activation as well as C-C coupling on the flat Co(0001) surface Revisited
Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 2016 Mechanisms of H- and OH-assisted CO activation as well as C-C coupling on
Synthesis of ethanol from paraformaldehyde, CO 2 and H 2
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Synthesis of ethanol from paraformaldehyde, CO 2 and
An Advanced Anode Material for Sodium Ion. Batteries
Layered-Structure SbPO 4 /Reduced Graphene Oxide: An Advanced Anode Material for Sodium Ion Batteries Jun Pan, Shulin Chen, # Qiang Fu, Yuanwei Sun, # Yuchen Zhang, Na Lin, Peng Gao,* # Jian Yang,* and
Design of Efficient Catalysts with Double Transition Metal. Atoms on C 2 N Layer
Supporting Information Design of Efficient Catalysts with Double Transition Metal Atoms on C 2 N Layer Xiyu Li, 1, Wenhui Zhong, 2, Peng Cui, 1 Jun Li, 1 Jun Jiang 1, * 1 Hefei National Laboratory for
Supporting Information
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2015 Supporting Information Are intramolecular frustrated Lewis pairs also intramolecular
Diastereoselective Synthesis of C2 -Fluorinated Nucleoside Analogues using an Acyclic Strategy
Supporting Information: Dostie, Prévost and Guindon S-1 Diastereoselective Synthesis of C2 -Fluorinated Nucleoside Analogues using an Acyclic Strategy Starr Dostie,, Michel Prévost *,, Philippe Mochirian,
Iodine-Mediated Chemical Vapor Deposition Growth of Metastable Transition Metal
Supporting Information Iodine-Mediated Chemical Vapor Deposition Growth of Metastable Transition Metal Dichalcogenides Qiqi Zhang,, Yao Xiao, #, Tao Zhang,, Zheng Weng, Mengqi Zeng, Shuanglin Yue, ± Rafael
A DFT study on the mechanism of the gas phase reaction of niobium with acetaldehyde
Indian Journal of Chemistry Vol. 51A, November 2012, pp. 1553-1560 A DFT study on the mechanism of the gas phase reaction of niobium with acetaldehyde Yong Wang a, b & Gui-hua Chen a, * a School of Pharmaceutical
Polymer Chemistry SUPPORTING INFORMATION
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Polymer Chemistry Thiol-Maleimide Click Chemistry: Evaluating the Influence of Solvent,
Supporting Information. Engineering the Composition and Crystallinity of Molybdenum Sulfide for High-performance Electrocatalytic Hydrogen Evolution
Supporting Information Engineering the Composition and Crystallinity of Molybdenum Sulfide for High-performance Electrocatalytic Hydrogen Evolution Yanpeng Li 1,2 *, Yifei Yu 2, Robert A. Nielsen 3, William
Two-Dimensional Carbon Compounds Derived from Graphyne with Chemical Properties Superior to Those of Graphene
Supplementary Information Two-Dimensional Carbon Compounds Derived from Graphyne with Chemical Properties Superior to Those of Graphene Jia-Jia Zheng, 1,2 Xiang Zhao, 1* Yuliang Zhao, 2 and Xingfa Gao
DFT Study on the Reaction of Molybdenum with Acetaldehyde in Gas Phase
Asian Journal of Chemistry; Vol. 25, No. 1 (2013), 89-94 http://dx.doi.org/10.14233/ajchem.2013.12753 DFT Study on the Reaction of Molybdenum with Acetaldehyde in Gas Phase YONG WANG 1,2 and GUO-LIANG
Supporting Information. DFT as a Powerful Predictive Tool in Photoredox Catalysis: Redox Potentials and Mechanistic Analysis
Supporting Information DFT as a Powerful Predictive Tool in Photoredox Catalysis: Redox Potentials and Mechanistic Analysis Taye B. Demissie,, Kenneth Ruud,, and Jørn. ansen *, Centre for Theoretical and
Supplementary Information:
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supplementary Information: Coordination and Insertion of Alkenes and Alkynes in Au III
Energy Profiles and Chemical Reactions
Energy rofiles and Chemical eactions + B C D E egensburg er-la Norrby Modeling Kinetics Molecular Modeling Stationary points Energies Barriers eaction rates DFT, ab initio, MM Ground & Transition states
ummary Manipulating Radicals
Manipulating Radicals ummary Modern catalysis research tries to address issues such as material scarcity, sustainability or process costs. One solution is to replace expensive and scarce noble metal catalysts
Organometallic Chemistry and Homogeneous Catalysis
rganometallic hemistry and omogeneous atalysis Dr. Alexey Zazybin Lecture N8 Kashiwa ampus, December 11, 2009 Types of reactions in the coordination sphere of T 3. Reductive elimination X-L n -Y L n +
Supplementary Figures
Supplementary Figures Supplementary Figure 1. DFT optimized structure of the [Ag III (L 1 )](ClO 4 ) 2 (1 ClO4 ) complex (CCDC code 978368). Hydrogen atoms and the two perchlorate anions have been omitted
Crystallographic Dependence of CO Activation on Cobalt Catalysts: HCP versus FCC
Crystallographic Dependence of CO Activation on Cobalt Catalysts: HCP versus FCC Jin-Xun Liu, Hai-Yan Su, Da-Peng Sun, Bing-Yan Zhang, and Wei-Xue Li* State Key Laboratory of Catalysis, Dalian Institute
Organometallic Catalysis
Organometallic Catalysis The catalysts we will study are termed homogeneous catalysts as they are dissolved in th e same solvent as the substrate. In contrast, heterogeneous catalysts, such as palladium
Ж У Р Н А Л С Т Р У К Т У Р Н О Й Х И М И И Том 50, 5 Сентябрь октябрь С
Ж У Р Н А Л С Т Р У К Т У Р Н О Й Х И М И И 2009. Том 50, 5 Сентябрь октябрь С. 873 877 UDK 539.27 STRUCTURAL STUDIES OF L-SERYL-L-HISTIDINE DIPEPTIDE BY MEANS OF MOLECULAR MODELING, DFT AND 1 H NMR SPECTROSCOPY
Functionalization of C(sp 3 ) H Bonds Using a Transient Directing Group
Literature eport Functionalization of C(sp 3 ) Bonds Using a Transient Directing Group eporter: Mu-Wang Chen Checker: Yue Ji Date: 2016-04-05 Yu, J.-Q. et al. Science 2016, 351, 252-256. Scripps esearch
Department of Chemistry, University of Rhode Island, Kingston, RI USA
Supporting Information for Controlled Organocatalytic Ring-Opening Polymerization of - Thionocaprolactone Partha P. Datta and Matthew K. Kiesewetter Department of Chemistry, University of Rhode Island,
The Study of Chemical Reactions. Mechanism: The complete, step by step description of exactly which bonds are broken, formed, and in which order.
The Study of Chemical Reactions Mechanism: The complete, step by step description of exactly which bonds are broken, formed, and in which order. Thermodynamics: The study of the energy changes that accompany
Catalytic performance of a dicopper-oxo complex for methane hydroxylation
Supporting Information Catalytic performance of a dicopper-oxo complex for methane hydroxylation Yuta Hori, Yoshihito Shiota, * Tomokazu Tsuji, Masahito Kodera, and Kazunari Yoshizawa * Institute for Materials
(%) benzene. benzene benzene
2nd International Conference on Machinery, Materials Engineering, Chemical Engineering and Biotechnology (MMECEB 2015) Mechanism of the Rhodium-Catalyzed Hydroformylation of 4-(1-phenylvinyl)pyridine:
Supporting Information
Supporting Information Uniformly Sized (112) Facet Co 2 P on Graphene for Highly Effective Photocatalytic Hydrogen Evolution Bin Tian, a, b Zhen Li, a, b Wenlong Zhen c and Gongxuan Lu *a a State Key Laboratory
Mechanistic Studies of Wacker-Type Amidocyclization. and Stereochemical Implications of Proton Transfer
Supporting Information Mechanistic Studies of Wacker-Type Amidocyclization of Alkenes Catalyzed by (IMes)Pd(TFA) 2 (H 2 O): Kinetic and Stereochemical Implications of Proton Transfer Xuan Ye, Paul B. White
Supporting Information
Supporting Information Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of ( )-11 -Hydroxycurvularin Hyeonjeong Choe, Thuy Trang Pham,
Supporting Information
Supporting Information Direct Chemical Vapor Deposition-Derived Graphene Glasses Targeting Wide Ranged Applications Jingyu Sun, Yubin Chen, Manish Kr. Priydarshi, Zhang Chen, Alicja Bachmatiuk,, Zhiyu
Lecture 14 (10/18/17) Lecture 14 (10/18/17)
Lecture 14 (10/18/17) Reading: Ch6; 190-191, 194-195, 197-198 Problems: Ch6 (text); 7, 24 Ch6 (study guide-facts); 4, 13 NEXT Reading: Ch6; 198-203 Ch6; Box 6-1 Problems: Ch6 (text); 8, 9, 10, 11, 12,
A DFT study on the NHC catalysed Michael addition of enols to α,βunsaturated acyl-azoliums. A base catalysed C-C bond-formation step.
A DFT study on the NHC catalysed Michael addition of enols to α,βunsaturated acyl-azoliums. A base catalysed C-C bond-formation step. Supporting Information Luis R. Domingo, a * José A. Sáez b and Manuel
Supporting Information
Supporting Information Electronic Origins of the Variable Efficiency of Room-Temperature Methane Activation by Homo- and Heteronuclear Cluster Oxide Cations [XYO 2 ] + (X, Y = Al, Si, Mg): Competition
SERS and NMR Studies of Typical Aggregation-induced. Emission Molecules
Supplemental information SERS and NMR Studies of Typical Aggregation-induced Emission Molecules Cheng Fang, Yujun Xie, Martin R. Johnston, Yinlan Ruan, Ben Zhong Tang 5, *, Qian Peng, *, Youhong Tang 6,
A dominant homolytic O-Cl bond cleavage with low-spin triplet-state Fe(IV)=O formed is revealed in the mechanism of heme-dependent chlorite dismutase
Supplementary Information to: A dominant homolytic O-Cl bond cleavage with low-spin triplet-state Fe(IV)=O formed is revealed in the mechanism of heme-dependent chlorite dismutase Shuo Sun, Ze-Sheng Li,
Supporting Infromation
Supporting Infromation Aromatic Triazole Foldamers Induced by C H X (X = F, Cl) Intramolecular Hydrogen Bonding Jie Shang,, Nolan M. Gallagher, Fusheng Bie,, Qiaolian Li,, Yanke Che, Ying Wang,*,, and
A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles
![A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles](/thumbs/91/105588880.jpg "A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles")
A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles Yong Yao, a Min Xue, a Xiaodong Chi, a Yingjie Ma, a Jiuming e, b Zeper Abliz, b and Feihe uang a,
1. Determine the oxidation state of the metal centre and count the number of electrons.
Exercise sheet : Organometallic chemistry Gunnar Bachem 1. Determine the oxidation state of the metal centre and count the number of electrons. 2. The metal fragment 1 reacts with the amine to give a carbene
Catalytic Nitrogen Fixation via Direct Cleavage of Nitrogen Nitrogen Triple Bond of Molecular Dinitrogen under Ambient Reaction Conditions
Catalytic Nitrogen Fixation via Direct Cleavage of Nitrogen Nitrogen Triple Bond of Molecular Dinitrogen under Ambient Reaction Conditions Kazuya Arashiba, Aya Eizawa, Hiromasa Tanaka, Kazunari Nakajima,
Catalysis Lectures W.H. Green 5.68J/10.652J Spring Handouts: Norskov et al., J. Catalysis Imbihl and Ertl, Chem. Rev. (partial) Homework
Catalysis Lectures W.H. Green 5.68J/10.652J Spring 2003 Handouts: Norskov et al., J. Catalysis Imbihl and Ertl, Chem. Rev. (partial) Homework Major points: 1) Why reactions have barriers, and how catalysts
5 The effect of steric bulk on C C bond activation
5 The effect of steric bulk on C C bond activation Inspired by: Willem-Jan van Zeist, Joost N. P. van Stralen, Daan P. Geerke, F. Matthias Bickelhaupt To be submitted Abstract We have studied the effect
NMR and IR spectra & vibrational analysis
Lab 5: NMR and IR spectra & vibrational analysis A brief theoretical background 1 Some of the available chemical quantum methods for calculating NMR chemical shifts are based on the Hartree-Fock self-consistent
TECHNIQUES TO LOCATE A TRANSITION STATE
32 III. TECHNIQUES TO LOCATE A TRANSITION STATE In addition to the location of minima, the calculation of transition states and reaction pathways is an interesting task for Quantum Chemistry (QC). The
Mechanism of Cu/Pd-Catalyzed Decarboxylative Cross-Couplings: A DFT Investigation
Mechanism of Cu/Pd-Catalyzed Decarboxylative Cross-Couplings: A DFT Investigation Andreas Fromm, a Christoph van Wüllen, b Dagmar Hackenberger a and Lukas J. Gooßen* a a Fachbereich Chemie Organische Chemie
by Iridium Silyl Complexes
Facile Redistribution of Trialkyl Silanes Catalyzed by Iridium Silyl Complexes Sehoon Park, Bong Gon Kim, Inigo Göttker-Schnetmann, and Maurice Brookhart*, Department of Chemistry, University of North
SUPPORTING INFORMATION
SUPPORTING INFORMATION Difunctionalization of Styrenes with Perfluoroalkyl and tert- Butylperoxy Radicals: Room Temperature Synthesis of (1- (tert-butylperoxy)-2-perfluoroalkyl)ethylbenzene Erbo Shi, Jiajun
Supporting Information. Gold Catalyzed β Regioselective Formal [3+2] Cycloaddition of. Ynamides with Pyrido[1,2 b]indazoles: Reaction Development
![Supporting Information. Gold Catalyzed β Regioselective Formal [3+2] Cycloaddition of. Ynamides with Pyrido[1,2 b]indazoles: Reaction Development](/thumbs/91/107313745.jpg "Supporting Information. Gold Catalyzed β Regioselective Formal [3+2] Cycloaddition of. Ynamides with Pyrido[1,2 b]indazoles: Reaction Development")
Supporting Information Gold Catalyzed β Regioselective Formal [+] Cycloaddition of Ynamides with Pyrido[, b]indazoles: Reaction Development and Mechanistic Insights Yinghua Yu, a Gui Chen, a Lei Zhu, a
Optimal Performance for Solar Thermal Power System
Energy and Power Engineering, 2009, 110-115 doi:10.4236/epe.2009.12017 Published Online November 2009 (http://www.scirp.org/journal/epe) Optimal Performance for Solar Thermal Power System Jianfeng LU 1,
Efficient Synthesis of Ethanol from CH 4 and Syngas on
Efficient Synthesis of Ethanol from CH 4 and Syngas on a Cu-Co/TiO 2 Catalyst Using a Stepwise Reactor Zhi-Jun Zuo 1, Fen Peng 1,2, Wei Huang 1,* 1 Key Laboratory of Coal Science and Technology of Ministry
Electronic Supplementary Information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Electronic Supplementary Information
SUPPLEMENTARY INFORMATION. Observation of tunable electrical bandgap in large-area twisted bilayer graphene synthesized by chemical vapor deposition
SUPPLEMENTARY INFORMATION Observation of tunable electrical bandgap in large-area twisted bilayer graphene synthesized by chemical vapor deposition Jing-Bo Liu 1 *, Ping-Jian Li 1 *, Yuan-Fu Chen 1, Ze-Gao
Chemistry 4021/8021 Computational Chemistry 3/4 Credits Spring Semester 2013 ( Due 4 / 10 / 12 )
Chemistry 4021/8021 Computational Chemistry 3/4 Credits Spring Semester 2013 ( Due 4 / 10 / 12 ) This problem set will take longer than the last one in the sense that you will almost certainly need to