Studies in the Sulfone Series. VIII. Infrared Absorption Spectra and Structure of Some Substituted Diphenyl Sulfones and Sulfoxides

Amstutz, E. D.; Hunsberger, I. Moyer; Chessick, J. J.

doi:10.1021/ja01147a102

Cited by 43 publications

(13 citation statements)

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“…The infrared spectrum of the natural mixture, as a paste in medicinal paraffin (Nujol) or in carbon disulphide solution, showed no band in the range 3100-3500 cm.-'. This recalls the similar behaviour of 1-nitroso-2-naphthol (Amstutz, Hunsberger & Chessick, 1951). Another tautomeric form (XII) was suggested for the 2-methyl compound by McCluskey (1922), because a dibenzoate could be obtained.…”

Section: Results and Experimentalsupporting

confidence: 81%

Structure of a naturally occurring antagonist of dihydrostreptomycin

Cornforth

James

1956

Biochemical Journal

107

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Section: Results and Experimentalsupporting

confidence: 81%

Structure of a naturally occurring antagonist of dihydrostreptomycin

Cornforth

James

1956

Biochemical Journal

107

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“…A possible explanation of this phenomenon seems to be that in all these orthoaldehydes which show an unusual high C-H frequency there exists a new and unusual kind of hydrogen bonding between the aldehydic hydrogen atom, which according to Walsh (32) possesses a partial positive charge (in contradistinction to an ordinary hydrogen atom bound to a carbon atom), and a nucleophilic acceptor in the ortho position, or near it. Such an acceptor can be a chlorine atom which, for example, forms hydrogen bonds in o-chlorophenol (31), etc., an etheric oxygen atom (11), or an oxygen atom of a nitro group (2,24).…”

Section: Discussionmentioning

confidence: 99%

Infrared Absorption of Aldehydic C--H Group

Pinchas¹

1955

Anal. Chem.

103

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Various aldehydes, substituted benzaldehydes in particular, were measured in the 3000to 2600-cm.-1 region. The aldehydic C-H group usually absorbs at about 2720 cm.'1, but in the case of some orthosubstituted benzaldehydes this band rises considerably.This effect is tentatively attributed to a new kind of hydrogen bonding involving the polar aldehydic hydrogen atom.Other characteristic bands in this region were also observed and their origin is discussed. These bands are of much value in elucidating the structure of substituted benzaldehydes. ACCORDING to Linnett's calculations ( 23), the force con-L stants of the aldehydic C-H bonds in acetaldehyde and formaldehyde are appreciably lower than those of the C-H bonds in both saturated and unsaturated hydrocarbons. This

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“…of a chloroform solution (3 mg. of pigment per 1., contained in a 150 X 18 mm. test-tube) 5 drops of a saturated chloroform solution of dry HC1 gas was added.…”

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confidence: 99%