Substituent effects on the formation of sulfonyl cations from sulfonyl chlorides: Comparisons of solvolysis kinetic data with calculated gas phase energies

Journal of Physical Organic Chemistry

Volumn 20, Issue 12, 2007, Pages 1093-1101

  Bentley, T William ^a   Jones, Robert O ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

Bond dissociation energies; Enthalpies of formation; Kinetics; Solvolysis; Substituent effects; Sulfonyl cations; Sulfonyl chlorides

Indexed keywords

CHEMICAL BONDS; CHLORINE COMPOUNDS; ENTHALPY; KINETICS; PROTONS; RATE CONSTANTS;

BOND DISSOCIATION ENERGIES; ENTHALPIES OF FORMATION; SUBSTITUENT EFFECTS; SULFONYL CHLORIDES;

POSITIVE IONS;

EID: 36749018649     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1262     Document Type: Article

References (66)

1. (a) Gal J-F, Maria P-C. Prog. Phys. Org. Chem. 1990; 17: 159-238;
2. (b) Bagno A, Scorrano G, More O'Ferrall RA. Reviews of Chemical Intermediates, vol. 7. Elsevier: Amsterdam, 1987; 313-352.
3. (a) Abboud J-LM, Herreros M, Notario R, Lomas JS, Mareda J, Müller P, Rossier J-C. J. Org. Chem. 1999; 64: 6401-6410;
4. (b) Abboud J-LM, Alkorta I, Davalos JZ, Müller P, Quintanilla E, Rossier J-C. J. Org. Chem. 2003; 68: 3786-3796.
5. (a) Bentley TW, Roberts I. J. Phys. Org. Chem. 2005; 18: 96-100;
6. (b) Bentley TW, Carter GE. J. Am. Chem. Soc. 1982; 104: 5741-5747;
7. (c) Kevill DN, Anderson SW. J. Am. Chem. Soc. 1986; 108: 1579-1585;
8. (d) Benutley TW, Garley MS. J. Phys. Org. Chem. 2006; 19: 341-349;
9. (e) Fry JL, Harris JM, Bingham RC, Schleyer PvR. J. Am. Chem. Soc. 1970; 92: 2540-2542.
10. (a) Nakata K, Fujio M, Nishimoto K, Tsuno Y. J. Phys. Org. Chem. 2003; 16: 323-335;
11. (b) DiLabio GA, Ingold KU. J. Org. Chem. 2004; 69: 1620-1624.
12. Bentley TW, Harris HC. J. Chem. Soc., Perkin Trans. 2 1986; 619-624.
13. Brown HC, Okamoto Y. J. Am. Chem. Soc. 1958; 80: 4979-4987.
14. Liu K-T, Chen H-I. J. Chem. Soc., Perkin Trans. 2 2000; 893-898.
15. Krygowski TM, Cyrañsky MK, Sung DD, Stepieñ BT. J. Phys. Org. Chem. 2004; 17: 699-706.
16. (a) Forbes RM, Maskill H. J. Chem. Soc., Chem. Comm. 1991; 854-856;
17. (b) Bentley TW, Koo IS, Llewellyn G, Norman SJ. Croat. Chem. Acta 1992; 65: 575-583;
18. (c) Bonifáci R, Forbes RM, Henderson R, Maskill H, Palou J, Richardson HL, Votsmeier M. Gazz. Chim. Ital. 1995; 125: 569-575;
19. (d) Thea S, Carpanelli C, Cevasco G. Eur. J. Org. Chem. 2001; 151-154;
20. (e) Thea S, Vigo D, Cevasco G. J. Chem. Soc., Perkin Trans. 2 2002; 611-614.
21. (a) Liebman JK. In The Chemistry of Sulphonic Acids, Esters and Their Derivatives (Chapter 8), Patai S, Rappoport Z (eds). Wiley: Chichester, 1991.;
22. (b) Guthrie JP, Gallant RT. Can. J. Chem. 2000; 78: 1295-1298.
23. (a) Fogleman EA, Koizumi H, Kercher JP, Sztáray B, Baer T. J. Phys. Chem. A 2004; 108: 5288-5294;
24. (b) Chatgilialoglu C, Griller D, Kanabus-Kaminska JM, Lossing FP. J. Chem. Soc., Perkin Trans. 2 1994; 357-360;
25. (c) Frank AJ, Turecek F. J. Phys. Chem. A 1999; 103: 5348-5361.
26. Hunter EP, Lias SG. J. Phys. Chem. Ref. Data 1998; 27: 413-656.
27. (a) Szulejko JE, McMahon TB. J. Am. Chem. Soc. 1993; 115: 7839-7848;
28. (b) Munson B, Smith D, Polley C. Int. J. Mass Spectrom. Ion Phys. 1977; 25: 323-326;
29. (c) Pommerening CA, Bachrach SM, Sunderlin LS. J. Am. Soc. Mass Spectrom. 1999; 10: 856-861.
30. Bentley TW, Harris HC, Ryu ZH, Lim GT, Sung DD, Szajda SR. J. Org. Chem. 2005; 70: 8963-8970.
31. Curtiss LA, Raghavachari K, Redfern PC, Rassolov V, Pople JA. J. Chem. Phys. 1998; 109: 7764-7776.
32. NIST website accessed in November 2006.
33. Fox JM, Dmitrenko O, Liao L, Bach RD. J. Org. Chem. 2004; 69: 7317-7328.
34. Bentley TW, Llewellyn G, McAlister JA. J. Org. Chem. 1996; 61: 7927-7932.
35. Schreiner PR. In The Investigation of Organic Reactions and Their Mechanisms (Chapter 7), Maskill H (ed.). (a) p. 242; (b) p. 119; (c) pp. 141-143. Blackwell: Oxford, 2006.
36. Koch W, Holthausen MC. A Chemist's Guide to Density Functional Theory. Wiley-VCH: Weinheim, 2000.
37. Cox JD, Pilcher G. Thermochemistry of Organic and Organometallic Compounds. Academic Press: London, 1970.
38. Bauschlicher CW, Jr. Chem. Phys. Lett. 1995; 246: 40-44.
39. (a) Bentley TW, Jones RO, Koo IS. J. Chem. Soc., Perkin Trans. 2 1994; 753-759;
40. (b) Bentley TW, Koo IS. J. Chem. Soc., Perkin Trans. 2 1989; 1385-1392;
41. (c) Bentley TW, Jones RO. J. Chem. Soc., Perkin Trans. 2 1993; 2531-2537;
42. (d) Koo IS, Bentley TW, Llewellyn G, Yang K. J. Chem. Soc., Perkin Trans. 2 1991; 1175-1179;
43. (e) Koo IS, Bentley TW, Kang DH, Lee I. J. Chem. Soc., Perkin Trans. 2 1991; 175-179.
44. Basch H, Hoz T. In The Chemistry of Sulphonic Acids, Esters and Their Derivatives (Chapter 1), Patai S, Rappoport Z (eds). Wiley: Chichester, 1991.
45. Párkányi L, Besenyei G. J. Mol. Struct. 2004; 691: 97-106.
46. (a) Ruttink PJA, Burgers PC, Francis JT, Terlouw JK. J. Phys. Chem. 1996; 100: 9694-9697;
47. (b) Ruttink PJA, Burgers PC, Trikoupis MA, Terlouw JK. Chem. Phys. Lett. 2001; 342: 447-451;
48. (c) Ventura ON, Kieninger M, Denis PA, Cachau RE. Chem. Phys. Lett. 2002; 355: 207-213.
49. Smith BJ, Radom L. J. Am Chem. Soc. 1993; 115: 4885-4888.
50. (a) For recent calculations and discussion on the reasons for the attenuation of solvent effects see Refs 4b and 28b.;
51. (b) Herrero R, Quintanilla E, Müller P, Abboud J-LM. Chem. Phys. Lett. 2006; 420: 493-496.
52. (a) Liu KT, Chen PS. J. Chem. Res. (S) 1994; 310-311.;
53. (b) Kevill DN, D'Souza MJ. J. Phys. Org. Chem. 1993; 6: 642-644.;
54. (c) Kevill DN, D'Souza MJ. J. Chem. Res. (S) 1993; 332-333.
55. (a) Kevill DN, D'Souza MJ. J. Phys. Org. Chem. 2002; 15: 881-888;
56. (b) Bentley TW, Carter GE, Harris HC. J. Chem. Soc., Perkin Trans. 2 1985; 983-990.
57. (a) Minegishi S, Kobayashi S, Mayr H. J. Am. Chem. Soc. 2004; 126: 5174-5181;
58. (b) Kevill DN. In Advances in Quantitative Structure-Energy Properties, Charton M (ed.). Jai Press: Greenwich, CT, 1996.;
59. (c) Schadt FL, Bentley TW, Schleyer PvR. J. Am. Chem. Soc 1976; 98: 7667-7674.
60. Bentley TW, Llewellyn G, Ryu ZH. J. Org. Chem. 1998; 63: 4654-4659.
61. Gordon IM, Maskill H, Ruasse M-F. Chem. Soc. Rev. 1989; 18: 123-151.
62. (a) Yang K, Koo IS, Lee I. J. Phys. Chem. 1995; 99: 15035-15040;
63. (b) Kislov VV, Ivanov SN. Russ. J. Gen. Chem. 2001;71:742- 751;
64. (c) Lee I, Kim CK, Li HG, Sohn CK, Kim CK, Lee HW, Lee B-S. J. Am. Chem. Soc. 2000; 122: 1162-11172.
65. Gaussian 03, Revision COl, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian, Inc., Wallingford CT, 2004.
66. Bentley TW, Gream GE. J. Org. Chem. 1985; 50: 1776-1778.