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Infrared and mass spectra of purine and substituted dihydropurines
Author(s) -
Connolly John S.,
Linschitz Henry
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090233
Subject(s) - chemistry , adduct , purine , mass spectrum , bond cleavage , infrared spectroscopy , molecule , bromide , deuterium , stereochemistry , hydrogen bond , medicinal chemistry , photochemistry , ion , organic chemistry , physics , quantum mechanics , enzyme , catalysis
Infrared spectra (potassium bromide) of purine, 7 (9)‐deuteriopurine, 6‐deuteriopurine, 8‐deuteriopurine and a number of substituted dihydropurines are presented. The latter compounds are the 6‐α‐hydroxyalkyl‐1,6 (or 3,6)dihydropurines formed by photoaddition of the respective alcohols to purine (4‐6). From the comparative spectra of purine and its mono‐deuterated derivatives, it is possible to make assignments of N‐H and N‐D stretching vibrations and tentative assignments of C‐H deformation modes. The spectra of the substituted dihydropurines show evidence of interesting hydrogen‐bonding interactions which are demonstrated most clearly in the distinct differences between the spectra of the diastereomeric purine‐ethanol adducts. Mass spectra of these compounds all indicate progressive scission of HCN molecules from the principal radical‐ion. In the case of the photo‐adducts, HCN scission is preceded by scission at the site ( i.e. 6‐position) of alcohol addition to the purine ring.