SOLVATION AND METAL-ION EFFECTS ON STRUCTURE AND REACTIVITY OF PHOSPHORYL COMPOUNDS .1. BETA-SUBSTITUTED ALKYLPHOSPHONIC ESTERS

被引：21

作者：

BELCIUG, MP ^{[1
]}

MODRO, AM ^{[1
]}

MODRO, TA ^{[1
]}

WESSELS, PL ^{[1
]}

机构：

[1] UNIV PRETORIA,DEPT CHEM,PRETORIA 0002,SOUTH AFRICA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1992年 / 5卷 / 12期

关键词：

D O I：

10.1002/poc.610051203

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NMR spectroscopic and conformational analyses were performed for three beta-substituted beta-phenylethylphosphonic esters, PhCHXCH2PO3Me2 (X = OH, OMe, Cl) in five solvents and in acetone containing sodium and magnesium salts. Strong attractive interactions between the phosphoryl group and the oxygen-containing substituent X were demonstrated, and were shown to involve intramolecular hydrogen bonding, donor-acceptor O --> P effect and the chelation of a metal ion. These effects led to marked selectivity in the population of individual conformations of the phosphonates. The analogous intramolecular effects were found to be much weaker in the corresponding carboxylic ester systems.

引用

页码：787 / 794

页数：8

共 39 条

[11]

COHN M, 1962, J BIOL CHEM, V237, P176

[12] A NEW SYNTHESIS OF OLEFINS FROM CARBONYL COMPOUNDS AND PHOSPHONIC ACID BIS AMIDES [J].

COREY, EJ ;

KWIATKOW.GT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) :6816-&

[13]

DEBOLSTER MWG, 1983, TOPICS PHOSPHORUS CH, V11, P80

[14] METAL-ION CATALYSIS IN NUCLEOPHILIC DISPLACEMENT-REACTIONS AT CARBON, PHOSPHORUS, AND SULFUR CENTERS .1. CATALYSIS BY METAL-IONS IN THE REACTION OF PARA-NITROPHENYL DIPHENYLPHOSPHINATE WITH ETHOXIDE [J].

DUNN, EJ ;

BUNCEL, E .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (09) :1440-1448

[15] METAL-ION CATALYSIS IN NUCLEOPHILIC DISPLACEMENT-REACTIONS AT CARBON, PHOSPHORUS, AND SULFUR CENTERS .2. METAL-ION CATALYSIS IN THE REACTION OF PARA-NITROPHENYL DIPHENYLPHOSPHINATE WITH ALKALI-METAL PHENOXIDES IN ETHANOL [J].

DUNN, EJ ;

MOIR, RY ;

BUNCEL, E ;

PURDON, JG ;

BANNARD, RAB .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (10) :1837-1845

[16] CONFIGURATION OF STEROID BROMOKETONES .1. METHYL 4-BETA-BROMO-3-KETOCHOLANATE [J].

FIESER, LF ;

ETTORRE, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (07) :1700-1704

[17]

GAJDA T, 1990, SYNTHESIS-STUTTGART, P717

[18]

GORENSTEIN DG, 1984, PHOSPHORUS 31 NMR, P27

[19] STUDIES OF HYDROGEN BONDING .8. HYDROGEN-BOND ASSOCIATION BETWEEN PHENOL AND SULPHOXIDES AND NITROSO COMPOUNDS [J].

GRAMSTAD, T .

SPECTROCHIMICA ACTA, 1963, 19 (05) :829-834

[20] HYDROGEN BONDING .17. NMR STUDIES OF HYDROGEN BONDING OF PHENOL WITH SEVERAL PROTON ACCEPTORS [J].

GRAMSTAD, T ;

BECKER, ED .

JOURNAL OF MOLECULAR STRUCTURE, 1970, 5 (04) :253-&

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