Electronic Supplementary Information (ESI) Structure-Property Relationships in Protic Ionic Liquids: A. Thermochemical Study
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1 Electrnic Supplementry Mteril (ESI) fr Physicl Chemistry Chemicl Physics. This jurnl is the Owner Scieties 2017 Electrnic Supplementry Infrmtin (ESI) Structure-Prperty Reltinships in Prtic Inic Liquids: A Thermchemicl Study Jshu E. S. J. Reid,,b Filipe Agpit, c Crls E. S. Bernrdes, c Filmen Mrtins, c Adm J. Wlker, b Seishi Shimizu,,* nd Mnuel E. Mins d Piedde c,* Yrk Structurl Bilgy Lbrtry, Deprtment f Chemistry, University f Yrk, Heslingtn, Yrk, YO10 5DD, United Kingdm; E-mil: seishi.shimizu@yrk.c.uk b TWI Ltd., Grnt Prk, Gret Abingtn, Cmbridge, CB21 6AL, United Kingdm c Centr de Químic e Biquímic e Deprtment de Químic e Biquímic, Fculdde de Ciêncis, Universidde de Lisb, Lisb, Prtugl.; E-mil: memp@fc.ul.pt. KEYWORDS: Prtic Inic Liquids / enthlpy f vpriztin / enthlpy f frmtin / clrimetry / b- initi clcultins / W1-F12 / CCSD(T)-F12
2 pk nd Aqueus pk pk vlues vlues f precursr species HA nd f the cnjugted cid HB + f precursr species B, s well s their differences ( pk ), re presented in Tble S1. Tble S1. Vlues f pk nd pk t K used in this wrk. Species pk Species pk HOAc 4.756±0.002 [HDMBuA][OAc] 5.30±0.04 e [HDMBuA] ; b 10.1 b [HTMEDA][OAc] 3.94±0.44 e [HTMEDA] ; 9.14 c [HDMEtA][OAc] 4.35±0.02 [HDMEtA] ±0.02 d Reference 1; the uncertinty ws ssumed s tw units f the lst digit given in the dt surce. b Reference 2. c Reference 3. d Clculted frm the equtin: pk = (2.151±0.046) 10-2 T (r 2 = ) btined frm lest squres liner fit t the dt in reference 4 (T represents the temperture in K); the ssigned uncertinty is the liner interpltin uncertinty f pk t T = K. e Clculted using the men vlue f the tw published pk results given in this tble; uncertinty crrespnds t the men devitin.
3 Clvet-drp micrclrimetry Direct mesurements f the stndrd mlr enthlpies f vpriztin f the studied PILs nd their cnstituent mines were crried ut by Clvet-drp micrclrimetry, s described in the min text. Results re summrized in Tble S2. Tble S2. Stndrd specific enthlpy f vpriztin, vp h /J g -1, ines nd PILs btined by Clvet-drp micrclrimetry t K. Amines/PILs DMBuA TMEDA DMEtA [HDMBuA][OAc] [HTMEDA][OAc] [HDMEtA][OAc] M / g ml vp h / J g < vp h > / J g ± ± ± ± ± ± 2.14 < > / mv W ± (ver-ll) / J g vp H m / kj ml ± ± ± ± ± ± 0.7 3
4 Slutin Clrimetry m Indirect mesurements f H were perfrmed fllwing n dpttin f the prcedure previusly described by Vitrin et l. 5,6, vp s described in the min text. Results f the slutin clrimetry mesurements re summrized in Tble S3. Tble S3. Stndrd mlr enthlpies f slutin, H / kj ml -1, ines nd PILs t K. sl m Amines/PILs DMBuA TMEDA DMEtA [HDMBuA][OAc] [HTMEDA][OAc] [HDMEtA][OAc] Eqn 10 Eqn 8 m H / kj ml -1 sl < sl H 0 m > / kj ml
5 Cmputtinl Detils The individul cmpnents f the W1-F12 enthlpies re summrized in Tble S4. The gs-phse stndrd enthlpy f frmtin fr ech f the mines under study ws clculted frm the respective tmiztin rectin using the W1-F12 enthlpies, s described in the min text (Tble S5). The CCSD(T)-F12/3C(FIX)/cc-pVDZ-F12 energies nd enthlpies f cetic cid, mines, nd the gseus species resulting frm cmbintin ines with cetic cid re given in Tble S6. The crrespnding entrpies clculted by Sttisticl Mechnics, 7 using vibrtin frequencies btined by the DF-B3LYP-D3/cc-pVTZ methd nd scled by re listed in Tble S7. Tble S4. Cmpnents f the W1-F12 enthlpies. All dt in hrtree. SCF vl. CCSD vl. T cre-vlence reltivistic spin-rbit DBOC H(therml) b H ( K) c C H O N N,N-dimethylbutylmine N,N,N,N -tetrmethylethne-1,2-dimine N,N-dimethylethnl mine Dignl Brn-Oppenheimer crrectin. b Therml enthlpy crrectin t K. Includes the zer-pint vibrtinl energy. c Enthlpy t T = K nd p 0 = 1 br. Tble S5. Cntributin f ech cmpnent f the W1-F12 prcedure t the gs-phse stndrd mlr enthlpies f frmtin. All dt in kj ml 1. SCF vl. CCSD vl. T cre-vlence reltivistic spin-rbit DBOC H(therml) b H c t m f Hm d N,N-dimethylbutylmine ± 2.7 N,N,N,N -tetrmethylethne-1,2-dimine ± 2.8 N,N-dimethylethnl mine ± 1.8 Dignl Brn-Oppenheimer crrectin. b Therml enthlpy crrectin t K. Includes the zer-pint vibrtinl energy. c Enthlpy f tmiztin t T = K nd pº = 1 br. d Enthlpy f frmtin t T = K nd pº = 1 br. 5
6 Tble S6. CCSD(T)-F12/3C(FIX)/cc-pVDZ-F12 energies nd enthlpies. All dt in hrtree. energy H(therml) b H HOAc DMEtA TMEDA DMBuA [DMEtA][HOAc] [TMEDA][HOAc] [DMBuA][HOAc] CCSD(T)-F12/3C(FIX)/cc-pVTZ-F12 energy. b Therml enthlpy crrectin t K. Includes the zer-pint vibrtinl energy. c Enthlpy t T = K. Tble S7. Stndrd (pº = 1 br) mlr entrpies t K. S m /J K -1 ml -1 HOAc DMEtA TMEDA DMBuA [DMEtA][HOAc] [TMEDA][HOAc] [DMBuA][HOAc]
7 Stndrd Mlr Enthlpies f Frmtin f Gseus [HDMBuA] +, [HTMEDA] +, nd [HDMEtA] + The stndrd mlr enthlpies f frmtin f gseus [HDMBuA] +, [HTMEDA] +, nd [HDMEtA] + (Tble S6) were btined frm: H ([HB], g) + = H (B, g) + H + (H, g) PA(B) (S1) where H (B, g) nd PA(B) represent the stndrd mlr enthlpies f frmtin nd the prtn ffinities f the crrespnding neutrl mines, respectively (Tble S6), nd H + (H, g) = ±0.080 kj ml Tble S8. Stndrd mlr enthlpies f frmtin nd prtn ffinities ines t K. Species H (B, g) /kj ml -1 PA(B)/kJ ml -1 H ([HB] +, g) DMBuA 91.2± ±8.0 b 475.8±8.4 TMEDA 9.2± ±8.0 b 514.2±8.5 DMEtA 207.8± ±16.1 c 385.1±16.2 This wrk, see Tble 1 in text. b Frm reference 10. c Men vlue f the B3LYP/6-311+G** nd MP2/6-311+G**//B3LYP/6-311+G** vlues given in reference 11 nd crrespnding men devitin. 7
8 References 1 Hynes W. M., CRC Hndbk f Chemistry nd Physics, 97th Editin, M. M. Kreevy nd S.-W. Oh, J. Am. Chem. Sc., 1973, 95, R. L. Gustfsn nd A. E. Mrtell, J. Am. Chem. Sc., 1959, 81, R. J. Littel, M. Bs nd G. J. Knp, J. Chem. Eng. Dt, 1990, 35, J. Vitrin, C. E. S. Bernrdes nd M. E. Mins d Piedde, Phys. Chem. Chem. Phys., 2012, 14, J. Vitrin, F. Agpit, M. F. M. Piedde, C. E. S. Bernrdes, H. P. Dig, J. P. Lel nd M. E. Mins d Piedde, J. Chem. Thermdyn., 2014, 77, K. K. Irikur nd D. J. Frurip, Cmputtinl Thermchemistry. Predictin nd Estimtin f Mleculr Thermdynmics, ACS Sympsium Series N. 677, Wshingtn, M. K. Keshrwni, B. Bruer nd J. M. L. Mrtin, J. Phys. Chem. A, 2015, 119, R. L. Wgmn, D. D.; Evns, W. H.; Prker, V. B.; Schumm, R. H.; Hlw, I.; Biley, S. M.; Churney, K. L.; Nuttll, J. Phys. Chem. Ref. Dt, Suppl. 2, 1982, 11, E. P. Hunter nd S. G. Lis, J. Phys. Chem. Ref. Dt, 1998, 27, N. N. Chipnin, T. N. Aksmentv, S. N. Admvich, A. I. Albnv, A. N. Mirskv, R. G. Mirskv nd M. G. Vrnkv, Cmput. Ther. Chem., 2012, 985,
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