REACTIONS IN MONOLAYERS - THE OXIDATION OF THIOLS TO DISULFIDES

被引：13

作者：

AHMAD, J

ASTIN, KB

机构：

来源：

COLLOIDS AND SURFACES | 1990年 / 49卷 / 3-4期

关键词：

D O I：

10.1016/0166-6622(90)80110-P

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：

The oxidation of monomolecular films of 1-octadecanethiol to dioctadecyl disulfide by potassium hexacyanoferrate (III) has been examined at the air-liquid interface. Expanded film types (i.e., large areas/molecule of ca 0.61 nm2/molecule) are found to react faster than the compressed films, where the area/molecule was 0.19 nm2/molecule. This result has been ascribed to the difficulty of orienting the octadecyl side chains in the compressed thiol film to form the preferred skew conformation of the disulfide product. MNDO molecular orbital calculations have been performed on diethyl disulfide as a model system to assess the magnitude of this preference. © 1990.

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页码：281 / 287

页数：7

相关论文

共 9 条

[1] INFLUENCING REACTIVITY BY MONOLAYER COMPRESSION - AN ALCOHOL DEHYDRATION [J].

AHMAD, J ;

ASTIN, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8175-8178

[2] OXIDATION OF ALCOHOL MONOLAYERS BY CHROMIC-ACID [J].

AHMAD, J ;

ASTIN, KB .

LANGMUIR, 1988, 4 (03) :780-781

[3] CONFORMER SELECTION BY MONOLAYER COMPRESSION [J].

AHMAD, J ;

ASTIN, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7434-7435

[4] CONFORMATIONAL-ANALYSIS .117. METHYL-ETHYL-DISULFIDE - MOLECULAR MECHANICS AND MOLECULAR-ORBITAL CALCULATIONS [J].

ALLINGER, NL ;

KAO, J ;

CHANG, HM ;

BOYD, DB .

TETRAHEDRON, 1976, 32 (23) :2867-2873

[5] GROUND-STATES OF MOLECULES .38. MNDO METHOD - APPROXIMATIONS AND PARAMETERS [J].

DEWAR, MJS ;

THIEL, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :4899-4907

[6] INSTRUMENTATION FOR HANDLING MONOMOLECULAR FILMS AT AN AIR-WATER-INTERFACE [J].

FROMHERZ, P .

REVIEW OF SCIENTIFIC INSTRUMENTS, 1975, 46 (10) :1380-1384

[7]

Tarbell D. S., 1961, ORGANIC SULFUR COMPO, P97, DOI [10.1016/B978-1-4831-9982-5.50013-0, DOI 10.1016/B978-1-4831-9982-5.50013-0]

[8] CHEMICAL-REACTIONS IN MONOLAYER FILMS CHROMATOGRAPHY, A MULTICOMPARTMENT TROUGH, AND THE HYDROLYSIS OF SURFACTANT ESTER DERIVATIVES OF TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II)2+ [J].

VALENTY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :1-8

[9] LOW-FREQUENCY RAMAN-SPECTRA OF DIMETHYL, METHYL ETHYL, AND DIETHYL DISULFIDES, AND ROTATIONAL-ISOMERISM ABOUT THEIR CARBON-SULFUR BONDS [J].

VANWART, HE ;

CARDINAUX, F ;

SCHERAGA, HA .

JOURNAL OF PHYSICAL CHEMISTRY, 1976, 80 (06) :625-630