Nitrosonium-catalyzed decomposition of S-nitrosothiols in solution: A theoretical and experimental study

Journal of the American Chemical Society

Volumn 127, Issue 31, 2005, Pages 10917-10924

  Zhao, Yi Lei ^a   McCarren, Patrick R ^a   Houk, K N ^a   Choi, Bo Yoon ^b   Toone, Eric J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANTS; CATALYSIS; CATALYSTS; CHEMICAL BONDS; DECOMPOSITION; NITROGEN COMPOUNDS; OXIDATION; POSITIVE IONS; REACTION KINETICS; SUBSTITUTION REACTIONS; SULFUR;

CATALYTIC CYCLE; HOMOLYSIS; OXIDANTS; S-NITROSOTHIOLS;

ALCOHOLS;

ANTIOXIDANT; DIMER; DISULFIDE; NITRIC OXIDE; NITROSO DERIVATIVE; NITROSONIUM; OXIDIZING AGENT; S NITROSOTHIOL; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DECOMPOSITION; MOLECULAR STABILITY; NITROSATION; OXIDATION; STRUCTURE ANALYSIS;

CATALYSIS; NITRIC OXIDE; S-NITROSOTHIOLS; SOLUTIONS;

EID: 23744490764     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050018f     Document Type: Article

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24. +; at the B3LYP/ 6-31+G* level, the former is higher by 1.7 kcal/mol than the latter.
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27. The intramolecular transition state for rotation around the S-N bond can interconvert 4 and 5 (see Supporting Information). The activation free energies are +20.4 and +18.1 kcal/mol in gas phase and acetonitrile. respectively.
28. The activation energy of 27 kcal/mol is the free-energy maxima in the homolysis of RSNO. We also located a concerted bimolecular transition structure with a barrier of 36 kcal/mol (ΔH‡) and 45 kcal/mol (ΔG‡) in the gas phase.
29. Because of the flatness of the potential energy surface, no transition state is located for breaking and forming intermediates 16 and 17. The estimated activation energy, even in acetonitrile, is less than 3 kcal/mol with respect to the intermediate based on scanning calculations.
30. The energetic profiles of the elimination-addition, addition-elimination, and intramolecular rotation mechanisms for the isomerization between 4 and 5 are shown in the Supporting Information.
31. Attempts to achieve the diradicaloid transition state failed for the monotonic uphill potential surface. The estimated barrier for decomposition should be slightly lower than the reaction enthalpy of 10 kcal/mol because of favorable entropy changes.
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35. -1, comparing to CBS-QB3, which has been shown to work well for similar species previously.