A molecular orbital study of the reactions of sydnones

E. B. Roche; L. B. Kier

doi:10.1016/S0040-4020(01)82474-1

A molecular orbital study of the reactions of sydnones

E. B. Roche, L. B. Kier

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

MO calculations using the ω Hückel LCAO technique have been performed on several 3-alkylsdnones. Energy calculatioins permit predictions for protonation of the number 2 N-atom, nucleophilic attack at the number 5 C-atom, electrophilic attack at the number 4 C-atom, and free-radical attack at the number 4 C-atom. Supporting evidence for these predictions is discussed, and mechanisms of base- and acid-catalyzed hydrolysis are proposed.

Original language	English (US)
Pages (from-to)	1673-1685
Number of pages	13
Journal	Tetrahedron
Volume	24
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4020(01)82474-1
State	Published - 1968
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)82474-1

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title = "A molecular orbital study of the reactions of sydnones",

abstract = "MO calculations using the ω H{\"u}ckel LCAO technique have been performed on several 3-alkylsdnones. Energy calculatioins permit predictions for protonation of the number 2 N-atom, nucleophilic attack at the number 5 C-atom, electrophilic attack at the number 4 C-atom, and free-radical attack at the number 4 C-atom. Supporting evidence for these predictions is discussed, and mechanisms of base- and acid-catalyzed hydrolysis are proposed.",

author = "Roche, {E. B.} and Kier, {L. B.}",

note = "Funding Information: Acknowledgements-Thaeu thorsa cknowledget he support of NIH grant G-M 13100a nd NIH Pre-doctoralF ellowship 1-Fl-GM-23,852,OlAl.M r. DouglasF lecknero f The Ohio StateU niversityC om-puterC enteri s acknowledgefdo r his assistanai n programmationD. r. ThomasH . Browno f theC hemistry DepartmentU, niversityo l Illinois, ChicagoC ircle, assistedu s in severailt erationc onvergenap roblems. We wouM like to thank Mr. Haroki Brown, Departmento f MathematicsT, bc Ohio StateU niversity, for valuabled iscussions.",

year = "1968",

doi = "10.1016/S0040-4020(01)82474-1",

language = "English (US)",

volume = "24",

pages = "1673--1685",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "4",

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T1 - A molecular orbital study of the reactions of sydnones

AU - Roche, E. B.

AU - Kier, L. B.

N1 - Funding Information: Acknowledgements-Thaeu thorsa cknowledget he support of NIH grant G-M 13100a nd NIH Pre-doctoralF ellowship 1-Fl-GM-23,852,OlAl.M r. DouglasF lecknero f The Ohio StateU niversityC om-puterC enteri s acknowledgefdo r his assistanai n programmationD. r. ThomasH . Browno f theC hemistry DepartmentU, niversityo l Illinois, ChicagoC ircle, assistedu s in severailt erationc onvergenap roblems. We wouM like to thank Mr. Haroki Brown, Departmento f MathematicsT, bc Ohio StateU niversity, for valuabled iscussions.

PY - 1968

Y1 - 1968

N2 - MO calculations using the ω Hückel LCAO technique have been performed on several 3-alkylsdnones. Energy calculatioins permit predictions for protonation of the number 2 N-atom, nucleophilic attack at the number 5 C-atom, electrophilic attack at the number 4 C-atom, and free-radical attack at the number 4 C-atom. Supporting evidence for these predictions is discussed, and mechanisms of base- and acid-catalyzed hydrolysis are proposed.

AB - MO calculations using the ω Hückel LCAO technique have been performed on several 3-alkylsdnones. Energy calculatioins permit predictions for protonation of the number 2 N-atom, nucleophilic attack at the number 5 C-atom, electrophilic attack at the number 4 C-atom, and free-radical attack at the number 4 C-atom. Supporting evidence for these predictions is discussed, and mechanisms of base- and acid-catalyzed hydrolysis are proposed.

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U2 - 10.1016/S0040-4020(01)82474-1

DO - 10.1016/S0040-4020(01)82474-1

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SP - 1673

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JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

A molecular orbital study of the reactions of sydnones

Abstract

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