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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 08 A Novel Type of Organometallic -R-,-dihydro--,-benzoxazines with R = [M( -C )(CO) ] (M = Re or Mn) units. Experimental and Computational Studies of the Effect of the Substituent R on the Ring-Chain Tautomerism. Juan Oyarzo, a Ramón Bosque, b Patricia Toro, a Carlos P. Silva, c Rodrigo Arancibia, d Mercè Font-Bardía, e Vania Artigas, a Carme Calvis, f Ramon Messeguer, f A. ugo Klahn, a,* Concepción López b,* a Instituto de Química, Pontificia Universidad Católica de Valparaíso, Casilla 09, Valparaíso, Chile. b Secció de Química Inorgànica del Departament de Química Inorgànica i Orgànica, Facultat de Química, Universitat de Barcelona, Martí I Franquès -. E Barcelona, Spain. c Departamento de Química de los Materiales, Facultad de Química y Biología, Universidad de Santiago de Chile, Soft Matter Research-Technology Center, SMAT-C, Av. B. O iggins 6, Casilla 0, Correo, Santiago, Chile. d Laboratorio de Química Inorgánica y Organometálica, Departamento de Química Analítica e Inorgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Concepción, Chile. e Unitat de Difracció de Raig-X, Centres Científics i Tecnològics (CCiT), Universitat de Barcelona, Solé i Sabaris, -, E-0808-Barcelona, Spain. f Biomed Division, ealth & Biomedicine Unit, LEITAT Technological Center, Parc Científic de Barcelona, Edifici èlix, Baldiri i Reixach -, E-0808-Barcelona, Spain. Supporting Information (7 pages)
2 Supporting information contents:.- Supplementary Figures Figure S. A) igh resolution mass spectrum (RMS) and B) electron impact mass spectrum of the solid isolated in the reaction between [Re( -C -CO)(CO) ] and the - aminobenzylalcohol. This product was identified by X-ray crystal diffraction as 6c (see text). Figure S. IR spectrum of compound 6c. Figure S. -NMR spectrum (in CDCl ) of the raw material isolated in the reaction between equimolar amounts of [Mn( -C -CO)(CO) ] and the -aminobenzylalcohol in refluxing benzene for h, showing the coexistence of several products. The expansion of the low field region shows the signals due to the protons of the aldehyde and the imine forms. The broad resonance in the range.< <.0 indicates the presence of the amine; while the typical pattern of the resonances due to the O C protons of the closed form, that appear as a doublet of doublets are also detected between.6 and. ppm (see inset on the right hand side). Figure S. A) igh resolution mass spectrum (RMS) and B) electron impact mass spectrum of compound 6d (see text). Figure S. IR spectrum of compound 6d. Figure S6. Atom numbering scheme for NMR studies. Figure S7. -NMR spectrum of compound 6c (in acetonitrile-d at 98 K). Expansion of selected regions of the spectrum are also presented in order to include the assignments of the resonances of the closed form (6c) and to show the coexistence of the imine form as a minor component. Signals marked with an asterisk are due to the imine form (c). Figure S8. -NMR spectrum of compound 6d (in acetonitrile-d at 98 K). Expansions of selected regions of the spectrum are included in order to include the assignments of the resonances of the closed form (6d) and to show the coexistence of the imine form as a minor component. Signals marked with purple asterisk are due to the imine form (d). Figure S9. C{ }- NMR spectrum of compound 6c in acetonitrile-d at 98 K. Figure S0. C{ }- NMR spectrum of compound 6d in acetonitrile-d at 98 K.
3 Figure S. [ - ]-NOESY spectrum of compound 6c in acetonitrile-d at 98 K. Figure S. [ - ]-NOESY spectrum of compound 6d in acetonitrile-d at 98 K. Figure S. [ - C]-SQC spectrum of compound 6c in acetonitrile-d at 98 K. Figure S. [ - C]-SQC spectrum of compound 6d in acetonitrile-d at 98 K. Figure S. [ - C]-MBC spectrum of compound 6c in acetonitrile-d at 98 K. Figure S6. [ - C]-MBC spectrum of compound 6d in acetonitrile-d at 98 K. Figure S7. -NMR spectrum of compound 6c (in CD Cl at 98 K) and an expansion of the spectrum showing the signal due to the imine proton of the open form (c). Figure S8. -NMR spectrum of compound 6d (in CD Cl at 98 K). Expansions of selected regions of the spectrum are included in order to show the signal due to the imine proton of the open form d and to ease the identification of the resonances and their assignment. Signals marked with an asterisk are due to the imine form d. Figure S9. (A) -NMR spectra of a freshly prepared solution of compound 6a in CD Cl and after different periods of storage (t = h, t = h at 98 K). (B) -NMR spectrum of the same sample after 0 h of storage at 98 K and an expansion showing the presence of a, 6a and ferrocenecarboxaldehyde. Figure S0. (A) -NMR spectrum of a freshly prepared solution of compound 6b in CD Cl at 98 and after different periods of storage (t = h, h at 98 K). (B) -NMR spectrum of the same sample after 0 h of storage at 98 K and an expansion showing the presence of b, 6b and benzaldehyde. Figure S. -NMR spectrum of compound 6c in benzene-d 6 at 98 K. Figure S. -NMR spectrum of compound 6d benzene-d 6 at 98 K. Figure S. C{ } -NMR spectra of compound 6c in (A) CD Cl or (B) in benzene-d 6 at 98 K. Figure S. C{ } -NMR spectra of compound 6d in (A) CD Cl or (B) in benzene-d 6 at 98 K. Figure S. -NMR spectrum of a freshly prepared solution of compound 6c in DMSO-d 6 at 98 and after different periods of storage (t). For t = 0 months the spectra showed additional resonances (marked with a yellow arrow) that indicate the presence of a minor component. Figure S6. -NMR spectrum of a freshly prepared solution of compound 6d in DMSO-d 6 at 98 and after different periods of storage (t).
4 Figure S7. -NMR and C{ } (bottom) NMR spectra (00 Mz) of the aldimine [Re{(η -C )- C=N-(C 6 --O)}(CO) ] (7c) in CDCl at 98 K. Figure S8. -NMR spectra (00 Mz) of the aldimine [Mn{(η -C )-C=N-(C 6 --O)}(CO) ] (7d) in CDCl at 98 K. Figure S9. -NMR spectra (00 Mz) of a freshly prepared solution of aldimine [Re{(η -C )- C=N-(C 6 --O)}(CO) ] (7c) in DMSO-d 6 at 98 K (top) and after different periods of storage (t) {t = h (middle) and h (bottom)}. Figure S0. -NMR spectra (00 Mz) of a freshly prepared solution of aldimine [Mn{(η -C )- C=N-(C 6 --O)}(CO) ] (7d) in DMSO-d 6 at 98 K (top) and after different periods of storage (t) {t = h (middle) and h (bottom)}. Figure S. UV-vis. spectra of compounds 6a-6d in C Cl at 98 K..- Supplementary Tables Table S. Crystal data and details of the refinement of the crystal structures of the -ferrocenyl,,-dihydro--,-benzoxazine (6a) and its -cyrhetrenyl- or -cymantrenylanalogues (6c and 6d, respectively). Table S. Final atomic coordinates for the optimized geometry of imine R-C=N-(C 6 --C O), [with R = ( -C )Fe( -C ), (a)]. Table S. Final atomic coordinates for the optimized geometry of imine R-C=N-(C 6 --C O)] [with R = Ph, (b)]. Table S. Final atomic coordinates for the optimized geometry of the R-C=N-(C 6 --C O) with R = Re( - C )(CO), (c). Table S. Final atomic coordinates for the optimized geometry of the R-C=N-(C 6 --C O) with R = Mn( - C )(CO), (d). Table S6. Final atomic coordinates for the optimized geometry of the -ferrocenyl,-dihydro- -,-benzoxazine (6a). Table S7. Final atomic coordinates for the optimized geometry of -phenyl,-dihydro--, benzoxazine (6b). Table S8. Final atomic coordinates for the optimized geometry of the -cyrhetrenyl,-dihydro- -,-benzoxazine compound (6c).
5 Table S9. Final atomic coordinates for the optimized geometry of the open form -cymanentryl,-dihydro--,-benzoxazine (6d). Table S0. Calculated distances between the imine nitrogen and atoms of the pendant O moiety in the imines R-C=N-(C 6 --C O) a-d, the Mulliken charges on the atoms involved in the 6-endo trig process and differences between their Mulliken charges. Table S. A) Calculated electronic energies (E in hartrees) for the imine forms R-C=N- (C 6 --C O) (a-d) and their corresponding: -R-,-dihydro--,- benzoxazines (6a-6d) in vacuum and in C Cl, and free energy (G) calculated for both tautomers at C under identical experimental conditions; B) Differences between the electronic energies ( E) and free energies ( G) (in kcal/mol) of the imine forms R-C=N-(C 6 --C O) (a-d) and those obtained for their corresponding tautomers -R-,-dihydro--, Benzoxazines (6a-6d), with the same R group, under identical conditions in vacuum and in C Cl and the calculated values of the free energy of the reactions 6 i i. Table S. Calculated energy (in ev) of the OMO and LUMO orbitals [E (OMO) and E (LUMO), respectively] and the energy gap [E gap = E (LUMO) - E (OMO) (in ev)] for the closed forms 6a-6d, shown below and Mulliken charges on selected atoms. Table S. Absorption spectroscopic data for -R-,-dihydro--,-benzoxazines (6a-6d) in C Cl at 98 K. Wavelengths ( i, in nm) and logarithms of the extinction coefficients (log i ( i in M - cm - )). a
6 .-SUPPLEMENTARY FIGURES Figure S. A) igh resolution mass spectrum (RMS) and B) electron impact mass spectrum of the solid isolated in the reaction between [Re( -C -CO)(CO) ] and the - aminobenzylalcohol. This product was identified by X-ray crystal diffraction as 6c (see text). A B 6
7 Figure S. IR spectrum of compound 6c. 7
8 Figure S. -NMR spectrum (in CDCl ) of the raw material isolated in the reaction between equimolar amounts of [Mn( -C -CO)(CO) ] and the -aminobenzylalcohol in refluxing benzene for h, showing the coexistence of several products. The expansion of the low field region shows the signals due to the protons of the aldehyde and the imine forms. The broad resonance in the range.< <.0 ppm indicates the presence of the amine; while the typical pattern of the resonances due to 7 protons of the -OC -unit of the closed form, (that appear as a doublet of doublets) are also detected between.6 and. ppm (see inset on the right hand side). 8
9 Figure S. A) igh resolution mass spectrum (RMS) and B) electron impact mass spectrum of compound 6d. A B 9
10 Figure S. IR spectrum of compound 6d. Figure S6. Atom numbering scheme for NMR studies (Green arrows indicate NOE peaks detected in the [ - ] NOESY spectra of compounds 6c and 6d in acetonitrile d solution at 98 K). closed form M OC CO OC N 6 8 N 7 O M Re (6c) Mn (6d) open form (imine) M OC CO OC 6 O 7 M Re (c) Mn (d) 0
11 Figure S7. -NMR spectrum of compound 6c (in acetonitrile-d at 98 K). Expansion of selected regions of the spectrum are also presented in order to include the assignments of the resonances of the closed form (6c) and to show the coexistence of the imine form as a minor component. Signals marked with an asterisk are due to the imine form (c). 6 Re OC OC CO 8 N O 7 (6c)
12 Figure S8. -NMR spectrum of compound 6d (in acetonitrile-d at 98 K). Expansions of selected regions of the spectrum are included in order to include the assignments of the resonances of the closed form (6d) and to show the coexistence of the imine form as a minor component. Signals marked with purple asterisk are due to the imine form (d). 6 Mn OC OC CO 8 N O 7 (6d)
13 Figure S9. C{ }-NMR spectrum of compound 6c (in acetonitrile-d at 98 K). Expansions of selected regions of the spectrum are shown to include the assignments of the resonances of the closed form (6c). 6 Re OC OC CO 8 N O 7 (6c)
14 Figure S0. C{ }-NMR spectrum of compound 6d (in acetonitrile-d at 98 K). Expansions of selected regions of the spectrum are shown in order to include the assignments of the resonances of the closed form (6d). 6 Mn OC OC CO 8 N O 7 (6d)
15 Figure S. [ - ]-NOESY spectrum of compound 6c in acetonitrile-d at 98 K. 6 >C-,, -OC - -N- -OC - >C-,, 6 Figure S. [ - ]-NOESY spectrum of compound 6d in acetonitrile-d at 98 K.
16 Figure S. [ - C]-SQC spectrum of compound 6c in acetonitrile-d at 98 K. Figure S. [ - C]-SQC spectrum of compound 6d in acetonitrile-d at 98 K 6
17 Figure S. [ - C]-MBC spectrum of compound 6c in acetonitrile-d at 98 K Figure S6. [ - C]-MBC spectrum of compound 6c in acetonitrile-d at 98 K 7
18 Figure S7. -NMR spectrum of compound 6c (in CD Cl at 98 K) and an expansion of the spectrum showing the signal due to the imine proton of the open form (c). 6 Re OC OC CO 8 N O 7 (6c) 8
19 Figure S8. -NMR spectrum of compound 6d (in CD Cl at 98 K). Expansions of selected regions of the spectrum are included in order to show the signal due to the imine proton of the open form d and to ease the identification of the resonances and their assignment. Signals marked with an asterisk are due to the imine form d 6 Mn OC OC CO 8 N O 7 (6d) 9
20 Figure S9. (A) -NMR spectra of a freshly prepared solution of compound 6a in CD Cl and after different periods of storage (t = h, t = h at 98 K). (B) -NMR spectrum of the same sample after 0 h of storage at 98 K and an expansion showing the presence of a, 6a and ferrocenecarboxaldehyde. (A) (B) 0
21 Figure S0. (A) -NMR spectrum of a freshly prepared solution of compound 6b in CD Cl at 98 and after different periods of storage (t = h, h) at 98 K. (B) -NMR spectrum of the same sample after 0 h of storage at 98 K and an expansion showing the presence of b, 6b and benzaldehyde. (A) (B)
22 Figure S. -NMR spectrum of compound 6c (in benzene-d 6 at 98 K). Expansions of selected regions of the spectrum are shown as insets together with the assignment of the resonances. 6 Re OC OC CO 8 N O 7 (6c)
23 Figure S. -NMR spectrum of compound 6d (in benzene-d 6 at 98 K). Expansions of selected regions of the spectrum are shown as insets together with the assignment of the resonances. 6 Mn OC OC CO 8 N O 7 (6d)
24 Figure S. C{ }-NMR spectra of compound 6c (A) in CD Cl and (B) in benzene-d 6 at 98 K.
25 Figure S. C{ } -NMR spectra of compound 6d (A) in CD Cl and (B) in benzene-d 6 at 98 K.
26 Figure S. -NMR spectrum of a freshly prepared solution of compound 6c in DMSO-d 6 at 98 and after different periods of storage (t). For t = 0 months the spectra showed additional resonances (marked with a yellow arrow) that indicate the presence of a minor component. 6
27 Figure S6. -NMR spectrum of a freshly prepared solution of compound 6d in DMSO-d 6 at 98 K and after different periods of storage (t). 7
28 Figure S7. (top) and C{ } (bottom) NMR spectra (00 Mz) of the aldimine [Re{(η -C )- C=N-(C 6 --O)}(CO) ] (7c) in CDCl at 98. Re OC OC CO N 6 O (7c) 8
29 Figure S8. -NMR spectra (00 Mz) of the aldimine [Mn{(η -C )-C=N-(C 6 --O)}(CO) ] (7d) in CDCl at 98 K. Mn OC OC CO N 6 O (7d) 9
30 Figure S9. -NMR spectra (00 Mz) of a freshly prepared solution of the aldimine [Re{(η - C )-C=N-(C 6 --O)}(CO) ] (7c) in DMSO-d 6 at 98 K and after different periods of storage (t). 0
31 Figure S0. -NMR spectra (00 Mz) of a freshly prepared solution of the aldimine [Re{(η - C )-C=N-(C 6 --O)}(CO) ] (7d) in DMSO-d 6 at 98 K and after different periods of storage (t).
32 Figure S. UV-visible spectra of C Cl solutions of the -R-,-dihydro--,-benzoxazines under study [R = ferrocenyl (6a), phenyl (6b) cyrhetrenyl (6c) and cymantrenyl (6d)] at 98 K.
33 .-SUPPLEMENTARY TABLES Table S. Crystal data and details of the refinement of the crystal structures of the -ferrocenyl,,-dihydro--,-benzoxazine (6a) and its -cyrhetrenyl- or -cymantrenyl- analogues (6c and 6d, respectively). 6a 6c 6d Crystal size a Empirical formula C 8 7 FeNO C 6 ReNO C 6 MnNO Formula weight 9.7() 68.7() 7.() Temperature (K) 70() 00() 00() (nm) Crystal system Monoclinic Orthorhombic Monoclinic Space group P Pna C/c a (Å).9().(7) 0.9() b (Å) 7.7() 6.6() 6.80() c (Å) 6.(7) 9.79().0() = (deg.) (deg.) 96.77() () V (Å ) 70.00() 8.7() 78.() Z 8 8 D calc. (Mg m - ) (mm - ) F(000) range for data collect. (deg.) Index ranges -7 h 7 from. to 6.6 from.6 to 9. from.70 to k 9-0 l 0 - h 9-8 k 6 - l - h -8 k 8 - l N. of collected reflect N. independent reflect. [R int ] Completeness to =. Absorption correct. Refinement method 9[0.08] 7[0.00] 08[0.0907] 99.6 % 99.7 % 99. % Semi-empirical from equivalents Full matrix least squares on F N. of data N. of parameters Goodness of fit on F Final R indices [I > (I)] R = 0.08, wr = R = 0.09, wr = R = 0.08, wr = 0.8
34 Final R indices (all data) R = 0.07, wr = 0.0 R = 0.09, wr = 0.08 R = , wr = 0.7 Absolute structure 0.0(8) 0.69(6) n/a parameter a (mm mm mm).
35 Table S. Final atomic coordinates for the optimized geometry of imine R-C=N-(C 6 --C O), [with R = ( -C )Fe( -C ), (a)] C C C C C C N C C C C C C C O Fe C C C C C
36 Table S. Final atomic coordinates for the optimized geometry of imine R-C=N-(C 6 -- C O)] (R = Ph, b). C N C C C C C C C O C C C C C C
37 Table S. Final atomic coordinates for the optimized geometry of the R-C=N-(C 6 --C O) (R = Re( -C )(CO), c). Re C C C C C C O C O C O C N C C C C C C C O
38 Table S. Final atomic coordinates for the optimized geometry of the R-C=N-(C 6 --C O) (R = Mn( -C )(CO), d) C C C C C C O C O C O C N C C C C C C C O Mn
39 Table S6. Final atomic coordinates for the optimized geometry of the -ferrocenyl,-dihydro- -,-benzoxazine (6a) C C C C C C N O C C C C C C C Fe C C C C C
40 Table S7. Final atomic coordinates for the optimized geometry of -phenyl,-dihydro--,- benzoxazine (6b). C N O C C C C C C C C C C C C C
41 Table S8. Final atomic coordinates for the optimized geometry of the -cyrhetrenyl,-dihydro- -,-benzoxazine (6c). Re C C C C C C O C O C O C N O C C C C C C C
42 Table S9. Final atomic coordinates for the optimized geometry of the open form -cymanentryl,-dihydro--,-benzoxazine (6d). Mn C C C C C C O C O C O C N O C C C C C C C
43 Table S0. Calculated distances between the imine nitrogen and atoms of the pendant O moiety in the imines R-C=N-(C 6 --C O) a-d, the Mulliken charges on the atoms involved in the 6-endo trig process and differences between their Mulliken charges. compound a b c d R = ferrocenyl phenyl cyrhetrenyl cymantrenyl O N N O Mulliken charges O C imine N Charge differences q C(imine) - q O q C (imine) - q N open forms (imines) 6 N R 7 O Fe Re OC OC CO Mn OC OC CO a b c d
44 Table S. A) Calculated electronic energies (E in hartrees) for the imine forms R-C=N-(C 6 --C O) (a-d) and their corresponding: -R-,-dihydro--,-benzoxazines (6a-6d) in vacuum and in C Cl, and free energy (G) calculated for both tautomers at C under identical experimental conditions; B) Differences between the electronic energies ( E) and free energies ( G) (in kcal /mol) of the imine forms R-C=N- (C 6 --C O) (a-d) and those obtained for their corresponding tautomers -R-,-dihydro--, benzoxazines (6a-6d), with the same R group, under identical conditions in vacuum and in C Cl and the calculated values of the free energy of the reactions 6 i i A) Electronic energy, (E) Free energy (G) In vacuum In C Cl In vacuum In C Cl R i Ferrocenyl a Phenyl b Cyrhenetryl c Cymantrenyl d
45 B) R and identification letter E = E(for i ) - E(for 6 i ) G = G(for i )-G(for 6 i ) G for the reaction 6 i i R i in vacuum In C Cl in vacuum In C Cl at 98 K, in C Cl Ferrocenyl a Phenyl b Cyrhenetryl c Cymantrenyl d
46 Table S. Calculated energy (in ev) of the OMO and LUMO orbitals [E (OMO) and E (LUMO), respectively] and the energy gap [E gap = E (LUMO) - E (OMO) (in ev)] for the closed forms 6a-6d, shown below and Mulliken charges on selected atoms. compound 6a 6b 6c 6d R = ferrocenyl phenyl cyrhetrenyl cymantrenyl E (OMO) E (LUMO) E gap Mulliken charges N C O Q C -Q O C closed forms 6 R 8 N O 7 6 Fe Re OC OC CO Mn OC OC CO 6a 6b 6c 6d 6
47 Table S. Absorption spectroscopic data for compounds in -R-,-dihydro--,- benzoxazines (6a-6d) in C Cl at 98 K. Wavelengths ( i, in nm) and logarithms of the extinction coefficients (log i ( i in M - cm - )]. a R identification log i log log log code Ferrocenyl 6a 0. 8 a. c. 8. Phenyl 6b 8 a.7 0 c.0 8. Cyrhetrenyl 6c Cymantrenyl 6d 08 b a See also Figure S; b according to the bibliography this band is attributed to metal to ligand charge transfer MLCT; c Broad; d Shoulder. 7
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