On the selenepin/benzene selenide valence tautomerizations: electronic and steric effects at theoretical levels

被引：3

作者：

Kassaee, M. Z. ^{[1
]}

Musavi, S. M. ^{[1
]}

Majdi, M. ^{[1
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

STRUCTURAL CHEMISTRY | 2009年 / 20卷 / 03期

关键词：

Selenepin; Benzene selenide; Valence tautomerization; Ab initio; DFT; DENSITY-FUNCTIONAL THEORY; X-RAY STRUCTURES; 1,3-SELENAZINE DERIVATIVES; ORGANOSELENIUM COMPOUNDS; VIBRATIONAL ANALYSIS; CRYSTAL-STRUCTURE; SELENONIUM SALT; AROMATICITY; BENZENE; ANTIBACTERIAL;

D O I：

10.1007/s11224-008-9396-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tautomerization in selenepin (1) benzenea double dagger OE selenide (2) binary system is found to favor, 2, at HF, MP2, and B3LYP levels, using 6-311G* basis set. Electronic effects appear to have small effects on 1a double dagger OE 2 equilibria and show little impact on the conformational ring inversions of 1, at the same levels. In contrast, steric effects effectively decrease a dagger H values in an order inversely proportional to the size of the substituents employed (Me > Et > i-Pr). A possible Se extrusion is suggested to be the main reason why no 2 has ever been detected experimentally.

引用

页码：369 / 376

页数：8

共 85 条

[41] Effective synthesis of 1,3-diselenole-2-selone-4,5-diselenolate (dsis) and its utilization for the synthesis of selenocycle-fused tetraselenafulvalene (TSF) derivatives [J].

Kodani, M ;

Takimiya, K ;

Aso, Y ;

Otsubo, T ;

Nakayashiki, T ;

Misaki, Y .

SYNTHESIS-STUTTGART, 2001, (11) :1614-1618

[42] 1,3-Selenazine derivatives induce cytotoxicity and DNA fragmentation in human HT-1080 fibrosarcoma cells [J].

Koketsu, M ;

Ishihara, H ;

Wu, WJ ;

Murakami, K ;

Saiki, I .

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 9 (02) :157-161

[43]

Koketsu M, 1998, RES COMMUN MOL PATH, V101, P179

[44]

Kwon O, 1999, J MOL STRUC-THEOCHEM, V460, P213, DOI 10.1016/S0166-1280(98)00319-4

[45]

Lamberth C., 2004, J SULFUR CHEM, V25, P39, DOI 10.1080/17415990310001612290

[46]

LARSEN DL, 1996, COMPREHENSIVE HETERO, V3, P475

[47]

Li JL, 1998, POL J CHEM, V72, P534

[48] Synthesis of phosphorus- and selenium-containing macrocycles and their complexation with Pd(II)Cl2 [J].

Li, JL ;

Meng, JB ;

Wang, YM ;

Wang, JT ;

Matsuura, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09) :1140-1146

[49] SYNTHESIS AND X-RAY STRUCTURE OF SELENASAPPHYRIN [J].

LISOWSKI, J ;

SESSLER, JL ;

LYNCH, V .

INORGANIC CHEMISTRY, 1995, 34 (13) :3567-3572

[50] Analysis of the origin of through-space proton NMR deshielding by selected organic functional groups [J].

Martin, NH ;

Brown, JD ;

Nance, KH ;

Schaefer, HF ;

Schleyer, PV ;

Wang, ZX ;

Woodcock, HL .

ORGANIC LETTERS, 2001, 3 (24) :3823-3826

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