Structure and spectroscopic characteristics of 4-tert-butylphenoxyacetylhydrazones of arylaldehydes.
By reaction of 4-tert-butylphenoxyacetylhydrazide with aromatic aldehydes and acetone a new series of 4-tert-butylphenoxyacetylhydrazones was synthesized. The structural peculiarities of the investigated molecules have been determined by means of X-ray analysis and IR spectroscopy. The diagnostically important IR spectral criteria required for the conformational analysis of acethylhydrazones have been considered. It was established that the 4-tert-butylphenoxyacetylhydrazide in condensed phase exists only as a ZN-C(O)-conformer. Its derivatives exist as EN-C(O) and ZN-C(O)-forms. As a rule, the prevalence of ZN-C(O)-form has been observed in CCl4 solutions. The structure of investigated compounds is also determined by a system of inter- and intramolecular hydrogen bonds. The energy of hydrogen bonds was estimated.
Podyachev
S N
SN
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of Russian Academy of Sciences, Arbuzov str. 8, 420088 Kazan, Russia. spodyachev@iopc.knc.ru
Litvinov
I A
IA
Shagidullin
R R
RR
Buzykin
B I
BI
Bauer
I
I
Osyanina
D V
DV
Avvakumova
L V
LV
Sudakova
S N
SN
Habicher
W D
WD
Konovalov
A I
AI
D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared
D001547:Benzaldehydes; D006835:Hydrazones