Rearrangement of substituted 11-phenyl-1H-dibenzo[b,e] [1,4]diazepin-1-one to dihydrophenazin-1-(2H)-one:: a theoretical approach

被引：3

作者：

Ramírez-G, G

Arroyo, MFR

Martínez, R

Angeles, E

机构：

[1] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico

[2] Univ Nacl Autonoma Mexico, Fac Estudios Super, Cuautitlan 54740, Izcalli, Mexico

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 1999年 / 489卷 / 01期

关键词：

AM1; calculation; frontier molecular orbitals and neighbors; reaction mechanism;

D O I：

10.1016/S0166-1280(99)00025-1

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

AM1 calculations were carried out to simulate the two possible pathways of the reaction of 3,3-dimethyl-11-phenyl-1H-dibenz[b,e] [1,4]diazepin-1-ones to 3,3-dimethyl-3,4-dihydrophenazin-1(2H)-ones in the presence of performic acid. Electronic properties and molecular orbitals were analyzed both at the beginning and during the reaction trajectory. Performic acid electrophilic reactivity is attributed to LUMO + I orbital. (C) 1999 Elsevier Science B.V. All rights reserved.

引用

页码：7 / 17

页数：11

共 15 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS
ALLINGER, NL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) : 8127 - 8134
[2] Bartlett P.D., 1950, REC CHEM PROG, V11, P47
[3] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL
DEWAR, MJS
ZOEBISCH, EG
HEALY, EF
STEWART, JJP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3902 - 3909
[4] FLEMING I, 1976, FRONTIER ORBITALS OR, P23
[5] GERSON CK, 1987, ANAL CHEM, V59, pA1031
[6] GUPTA RR, 1998, PHENOTHIAZINES 1 4 B
[7] BENZOFURAZAN OXIDE .2. REACTIONS WITH ENOLATE ANIONS
ISSIDORIDES, CH
HADDADIN, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 4067 - +
[8] KANEKO C, 1970, TETRAHEDRON LETT, P2329
[9] Martinez R, 1996, HETEROCYCL COMMUN, V2, P47
[10] OTTO AH, 1993, J MOL STRUCT, V285, P169

← 1 2 →