The Application of Bond Refractions to Organo-silicon Chemistry

Warrick, E. L.

doi:10.1021/ja01216a004

Cited by 73 publications

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“…These plots show clearly that the change in molecular refractivity effected by the introduction of a given atom into an organosilicon molecule depends to a marked extent on whether the new atom is attached to carbon or to silicon. This is striking evidence for the validity of the postulate by Denbigh (35) and Warrick (198) that bond refractivities are more generally applicable than atomic refractivities. Refraction of visible light depends upon the electronic polarizability of molecules, and for any atom this will vary as other atoms of different size and electronegativity are attached.…”

Section: A Density and Boiling Pointmentioning

confidence: 59%

Relationships between Analgous Organic Compounds of Silicon and Carbon.

Gilman¹,

Dunn²

1953

Chem. Rev.

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Section: A Density and Boiling Pointmentioning

confidence: 59%

Relationships between Analgous Organic Compounds of Silicon and Carbon.

Gilman¹,

Dunn²

1953

Chem. Rev.

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“…As a further check on the structure and identity of each compound, molecular refractions were calculated in two ways, first by means of the conventional N = -:-. Warrick (7).…”

mentioning

confidence: 99%

“…4. Molecular refractions of the various products were determined through the use of the Lorenz-Lorentz formula and by means of bond refraction values presented by Warrick (7).…”

mentioning

confidence: 99%

STUDIES IN SILICO-ORGANIC COMPOUNDS. VIII. THE PREPARATION AND PROPERTIES OF POLYETHERS FROM TRICHLOROSILANE, CONTINUED^{1, 2}

Joffe¹,

Post²

1949

J. Org. Chem.

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Hydrogen chloride has a definite part in this reaction as has been demonstrated in the course of this work and its predecessor (1). There was no action when triethoxysilane and ethyl alcohol were refluxed for twenty-four hours but when dry hydrogen chloride was passed through triethoxysilane at 80°a small amount of hydrogen was evolved and some triethoxychlorosilane formed. A mechanism has already been postulated (1).Hydrogen was also evolved with formation of tetraethoxysilane when dry hydrogen chloride was bubbled through a mixture of refluxing triethoxysilane and ethyl alcohol. Triethoxysilane and moist ethyl alcohol reacted on twentyfour hour reflux to form various hydrolysis products.To examine the effects of variation in radical size, possible differing effect of dissolved hydrogen chloride, and other factors, on these reactions, trichlorosilane was allowed to react separately with several different alcohols including phenol both with and without benzene as a solvent. Yields of trialkoxy-and tetraalkoxy-silanes are reported in Table I.In addition, the data already presented (1) with respect to ethyl, n-propyl, and n-butyl analogs were checked. ¿-Butyl alcohol led only to what was probably a polymerized 1,3-dioxodisiloxane, a hydrolysis product:Hydrolysis products also resulted from the interaction of allyl alcohol and trichlorosilane. Trialloxysilane polymerized at the boiling point, 188°( 760 mm). There was almost no evolution of hydrogen from the reaction using benzyl alcohol. After excess benzyl alcohol had been distilled from the reaction mixture, contact with sodium hydroxide showed the residue to be largely tribenzoxysilane. However, only tetrabenzoxysilane could be isolated on distillation. It has 1 The work on which this report is based comprises a part of a program of research carried out under contract with the Office of Naval Research.8 Submitted by the first author to the Graduate School of Arts and Sciences of the University of Buffalo in partial fulfillment of the requirements for the degree of Doctor of Philosophy.

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“…Tetrachlorosilane, trimethylchlorosilane, and other reagents were purchased from reputable sources and were found to have satisfactory physical constants. Molar refractions were calculated from the data of Warrick (5).…”

Section: Introductionmentioning

confidence: 99%

STUDIES IN SILICO-ORGANIC COMPOUNDS. XXVIII. THE PREPARATION OF p-TRIALKYLSILYLPHENYLCARBINOLS

Campagna¹,

Post²

1954

J. Org. Chem.

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The Application of Bond Refractions to Organo-silicon Chemistry

Cited by 73 publications

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Relationships between Analgous Organic Compounds of Silicon and Carbon.

Relationships between Analgous Organic Compounds of Silicon and Carbon.

STUDIES IN SILICO-ORGANIC COMPOUNDS. VIII. THE PREPARATION AND PROPERTIES OF POLYETHERS FROM TRICHLOROSILANE, CONTINUED^{1, 2}

STUDIES IN SILICO-ORGANIC COMPOUNDS. XXVIII. THE PREPARATION OF p-TRIALKYLSILYLPHENYLCARBINOLS

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The Application of Bond Refractions to Organo-silicon Chemistry

Cited by 73 publications

References 0 publications

Relationships between Analgous Organic Compounds of Silicon and Carbon.

Relationships between Analgous Organic Compounds of Silicon and Carbon.

STUDIES IN SILICO-ORGANIC COMPOUNDS. VIII. THE PREPARATION AND PROPERTIES OF POLYETHERS FROM TRICHLOROSILANE, CONTINUED1, 2

STUDIES IN SILICO-ORGANIC COMPOUNDS. XXVIII. THE PREPARATION OF p-TRIALKYLSILYLPHENYLCARBINOLS

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STUDIES IN SILICO-ORGANIC COMPOUNDS. VIII. THE PREPARATION AND PROPERTIES OF POLYETHERS FROM TRICHLOROSILANE, CONTINUED^{1, 2}