Bibliographic Details
| Title: |
Theoretical Study of Nucleophilic Substitution at the Disulfide Bridge of Cyclo-L-cystine. |
| Authors: |
Bachrach, Steven M., Chamberlin, Adam C. |
| Source: |
Journal of Organic Chemistry. 6/13/2003, Vol. 68 Issue 12, p4743. 5p. 3 Diagrams, 3 Charts. |
| Subjects: |
Nucleophilic reactions, Sulfonates |
| Abstract: |
The reaction of cyclo-L-cystine with thiolate is examined at the B3LYP/6-31+G[sup *] level. The two isomers of cyclo-l-cystine differ in their dihedral angle about the disulfide bond; the M isomer (with dihedral angle of -90.1°) is found to be slightly lower in energy. The nucleophilic substitution reaction at sulfur follows the addition-elimination mechanism, exemplified by the hypercoordinate sulfur intermediate on the reaction surface. The reaction is exergonic (ΔG = -6.16 kcal mol[sup -1]), and both the entrance and exit transition state lie below the reactant energies. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
