Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base

Masahiro Terada; Chikashi Kanazawa; Masahiro Yamanaka

Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base

Masahiro Terada, Chikashi Kanazawa, Masahiro Yamanaka

SCI - Chemistry

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

17 Citations (Scopus)

Abstract

Theoretical studies of the organic base-catalyzed 5-exo intramolecular cyclization of o-alkynylbenzoic acid were documented. The acidic fragment participating in the transition states was shown to reduce the activation energy significantly on the basis of hybrid DFT (BHandHLYP) calculation of 5-exo and 6-endo transition states. Furthermore, preference for the 5-exo cyclization mode was rationalized by natural population analysis of optimized structures of the transition states and the reactants.

Original language	English
Pages (from-to)	819-825
Number of pages	7
Journal	Heterocycles
Volume	74
Issue number	C
Publication status	Published - 2007 Dec 31

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base",

abstract = "Theoretical studies of the organic base-catalyzed 5-exo intramolecular cyclization of o-alkynylbenzoic acid were documented. The acidic fragment participating in the transition states was shown to reduce the activation energy significantly on the basis of hybrid DFT (BHandHLYP) calculation of 5-exo and 6-endo transition states. Furthermore, preference for the 5-exo cyclization mode was rationalized by natural population analysis of optimized structures of the transition states and the reactants.",

author = "Masahiro Terada and Chikashi Kanazawa and Masahiro Yamanaka",

year = "2007",

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T1 - Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base

AU - Terada, Masahiro

AU - Kanazawa, Chikashi

AU - Yamanaka, Masahiro

PY - 2007/12/31

Y1 - 2007/12/31

N2 - Theoretical studies of the organic base-catalyzed 5-exo intramolecular cyclization of o-alkynylbenzoic acid were documented. The acidic fragment participating in the transition states was shown to reduce the activation energy significantly on the basis of hybrid DFT (BHandHLYP) calculation of 5-exo and 6-endo transition states. Furthermore, preference for the 5-exo cyclization mode was rationalized by natural population analysis of optimized structures of the transition states and the reactants.

AB - Theoretical studies of the organic base-catalyzed 5-exo intramolecular cyclization of o-alkynylbenzoic acid were documented. The acidic fragment participating in the transition states was shown to reduce the activation energy significantly on the basis of hybrid DFT (BHandHLYP) calculation of 5-exo and 6-endo transition states. Furthermore, preference for the 5-exo cyclization mode was rationalized by natural population analysis of optimized structures of the transition states and the reactants.

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