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8‐Arylpurines and their ultraviolet absorption spectra
Author(s) -
Fu S.C. J.,
Chinoporos E.
Publication year - 1966
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.5570030418
Subject(s) - bathochromic shift , chemistry , molar absorptivity , substituent , ultraviolet , hyperchromicity , spectral line , absorption spectroscopy , ionic bonding , absorption (acoustics) , ionic strength , analytical chemistry (journal) , stereochemistry , organic chemistry , aqueous solution , optics , ion , dna , biochemistry , physics , astronomy , fluorescence
Dehydrocyclization of 4‐amino‐5‐arylamidopyrimidines in polyphosphoric acid to 8‐arylpurines was further investigated. Various other 8‐arylpurines were synthesized by this new procedure in high purity and yield. The ultraviolet absorption spectra of the arylpurines and the corresponding acylamidopyrimidines were measured at p H 1, 7, and 13 at 0.1 molar ionic strength. The spectra of the purines resemble those of the corresponding acylamidopyrimidines and, to a lesser extent, the corresponding 4,5‐diaminopyrimidines. The bathochromic shifts caused by different substituting groups in monosubstituted purines, in general, parallel the inductive effect of the substituting groups. The hyperchromicity and the inductive constant of the substituting groups assume a linear relationship, for substitution at either the 2 or 6 position. These changes in the wave length of maximum absorption and in the molar extinction coefficient caused by 2, 6 and 8 substitutions of the purines reported here are in agreement with previous studies by Mason.