An ab initio study of some heterocyclic 6 pi-carbenes

被引：40

作者：

Sauers, RR

机构：

[1] Department of Chemistry, Rutgers, Stt. Univ. of New Jersey, New Brunswick

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 02期

关键词：

D O I：

10.1016/0040-4039(95)02119-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ab initio calculations on a series of 6 pi-electron heterocyclic ring systems containing O, N, and S atoms provided evidence for aromatic stabilization ranging from 7.6 to 25.5 kcal/mol. The most highly stabilized system was the imidazolyl carbene which had an aromatic stabilization energy comparable to furan and pyrrole. Proton affinity data was consistent with literature pKa measurements of the conjugate acids.

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页码：149 / 152

页数：4

相关论文

共 22 条

[1] ELECTRON-DISTRIBUTION IN A STABLE CARBENE [J].

ARDUENGO, AJ ;

DIAS, HVR ;

DIXON, DA ;

HARLOW, RL ;

KLOOSTER, WT ;

KOETZLE, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6812-6822

[2]

Bernardi F., 1988, J MOL STRUCT, V163, P173

[3] CRYSTAL-STRUCTURE OF THE DIMERIC (4-TERT-BUTYLTHIAZOLATO)(GLYME)LITHIUM - CARBENE CHARACTER OF A FORMYL ANION EQUIVALENT [J].

BOCHE, G ;

HILF, C ;

HARMS, K ;

MARSCH, M ;

LOHRENZ, JCW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (04) :487-489

[4] ACIDITIES OF C2 HYDROGEN-ATOMS IN THIAZOLIUM CATIONS AND REACTIVITIES OF THEIR CONJUGATE BASES [J].

BORDWELL, FG ;

SATISH, AV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :985-990

[5]

BOYD GV, COMPREHENSIVE HET 4B, V6

[6] THE MECHANISM OF THIAMINE ACTION .2. RAPID DEUTERIUM EXCHANGE IN THIAZOLIUM SALTS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (07) :1762-1763

[7] GALLIUM-CONTAINING 6-PI-ELECTRON RING-SYSTEMS [J].

BROWN, DS ;

DECKEN, A ;

COWLEY, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5421-5422

[8] REACTION OF A STABLE SILYLENE WITH COVALENT AZIDES - A NEW SYNTHESIS FOR SILAIMINES [J].

DENK, M ;

HAYASHI, RK ;

WEST, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10813-10814

[9] ELECTRONIC-STRUCTURE OF A STABLE NUCLEOPHILIC CARBENE [J].

DIXON, DA ;

ARDUENGO, AJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (11) :4180-4182

[10]

DIXON DA, 1987, MOL STRUCTURE ENERGE, V2, pCH7