Disparate behavior of carbonyl and thiocarbonyl compounds: Acyl chlorides vs thiocarbonyl chlorides and isocyanates vs isothiocyanates

Journal of Organic Chemistry

Volumn 74, Issue 10, 2009, Pages 3659-3664

  Wiberg, Kenneth B ^a   Wang, Yi Gui ^a   Miller, Scott J ^a   Puchlopek, Angela L A ^a   Bailey, William F ^b   Fair, Justin D ^b  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ACTIVATION FREE ENERGY; ACYL CHLORIDES; ALCOHOL MOLECULES; ATOMIC CHARGE DISTRIBUTIONS; BENZOYL CHLORIDES; DEALKYLATION; HYDROGENOLYSIS REACTIONS; INFORMATION CONCERNING; ISOTHIOCYANATES; SIX-MEMBERED RINGS; THIOCARBONYL; THIOCARBONYL COMPOUNDS; TRANSITION STATE;

ACTIVATION ENERGY; CHARGE DISTRIBUTION; CHARGED PARTICLES; ETHANOL; HYDROGEN; METHANOL;

CHLORINE COMPOUNDS;

ALCOHOL; AMMONIUM DERIVATIVE; CARBONYL DERIVATIVE; ISOCYANIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEALKYLATION; ENERGY; HYDROGEN BOND; HYDROGENOLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

BENZOATES; ISOCYANATES; ISOTHIOCYANATES; KINETICS; SULFUR; THERMODYNAMICS;

EID: 65949098649     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9004316     Document Type: Article

References (28)

1. (a) Patai, S. Ed. The Chemistry of the Carbonyl Group; Interscience: New York, 1966.
2. (b) Mayer, R.; Scheithauer, S. In Methoden der Organischen Chemie; Georg Thieme: New York, 1985; Vol.5, pt. 2.
3. Hadad, C. M.; Rablen, P. R.; Wiberg, K. B. J. Org. Chem. 1998, 63, 8668.
4. Sanchez-Rosello, M.; Puchlopek, A. L. A.; Morgan, A. J.; Miller, S. J. J. Org. Chem. 2008, 73, 1774.
5. Norris, J. F.; Young, H. H., Jr. J. Am. Chem. Soc. 1935, 57, 1420.
6. Scheithauer, S.; Mayer, R. Chem. Ber. 1965, 98, 838.
7. (a) Hsu, F.-L.; Zhang, X.; Hong, S.-S.; Berg, F. J.; Miller, D. D. Heterocycles 1996, 39, 801.
8. (b) Millan, D. S.; Prager, R. H. Tetrahedron Lett. 1998, 39, 4387.
9. (c) Millan, D. S.; Prager, R. H. Aust. J. Chem. 1999, 52, 841.
10. -1) increase linearly with ethanol concentration, suggesting a second order dependence on the alcohol concentration. See, for example:
11. (b) Caraculacu, A. A.; Agherghinei, I.; Baron, P.; Timpu, D. Rev. Roum. Chim. 1996, 18, 725.
12. Rao, C. N. R.; Venkataraghavan, R. Tetrahedron 1962, 18, 531.
13. Staudinger, H.; Siegwart, J. Helv. Chim. Acta 1920, 3, 824.
14. Kata, S. Phosphorus, Sulfur, Silicon 1997, 120, 213.
15. Fersht, A. R.; Jencks, W. P. J. Am. Chem. Soc. 1970, 92, 5432;
16. J. Am. Chem. Soc. 1970, 92, 5442.
17. In the polarized continuum model, all solvents with a dielectric constant of 20 or greater will give approximately the same solvent effect.
18. (a) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
19. (b) Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 1999, 103, 9100.
20. (a) Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 129.
21. (b) Nalewajski, R. F.; Parr, R. G. Proc. Natl. Acad. Sci. 2000, 97, 8879.
22. (c) Parr, R. G.; Ayers, P. W.; Nalewajski, R. F. J. Phys. Chem. A, 2005, 109, 3957.
23. (a) Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
24. (b) Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1995, 117, 2201.
25. (a) Ungnade, H. E.; Nightingale, D. V. J. Am. Chem. Soc. 1944, 66, 1218.
26. (b) Leardini, R.; Zanardi, G. Synthesis 1982, 3, 225.
27. Frisch, M. J. ; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kundin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; 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, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortis, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian Development Version E; Gaussian, Inc.: Wallingford, CT, 2006.
28. Program written by P. R. Rablen, Ph.D. thesis, 1994.