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Theoretical Study of Nucleophilic Substitution at the Disulfide Bridge of Cyclo-L-cystine.

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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]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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Header DbId: egs
DbLabel: Engineering Source
An: 10077652
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  Data: Theoretical Study of Nucleophilic Substitution at the Disulfide Bridge of Cyclo-L-cystine.
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 6/13/2003, Vol. 68 Issue 12, p4743. 5p. 3 Diagrams, 3 Charts.
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  Data: 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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  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1021/jo034046x
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      – Code: eng
        Text: English
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        PageCount: 5
        StartPage: 4743
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      – SubjectFull: Nucleophilic reactions
        Type: general
      – SubjectFull: Sulfonates
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      – TitleFull: Theoretical Study of Nucleophilic Substitution at the Disulfide Bridge of Cyclo-L-cystine.
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              Text: 6/13/2003
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              Y: 2003
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              Value: 68
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