Selective deshielding of aromatic protons in some ortho-substituted acetanilides | Zendy

J. R. Bartels-Keith | Zendy; Ronald F. W. Cieciuch | Zendy

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Selective deshielding of aromatic protons in some ortho-substituted acetanilides

Author(s) -

J. R. Bartels-Keith,

Ronald F. W. Cieciuch

Publication year - 1968

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v68-422

Subject(s) - chemistry , acetanilide , intramolecular force , proton , hydrogen bond , nitro , proton magnetic resonance , solvent , sulfonyl , aromaticity , medicinal chemistry , photochemistry , proton nmr , stereochemistry , computational chemistry , molecule , organic chemistry , nuclear magnetic resonance , physics , alkyl , quantum mechanics

Certain ortho-substituted acetanilides exhibit proton magnetic resonance signals at unusually low field for the amido proton and the aromatic proton adjacent to the acetamido group. This effect, explicable in terms of intramolecular hydrogen-bonding, has been observed for nitro, carbonyl, sulfamoyl, and sulfonyl substituents. Solvent effects are discussed.

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