BENZENOID-QUINOID TAUTOMERISM OF SALICYLIDENIMINES: CRYSTAL STRUCTURES OF 5-BROMO- (HL1) AND 3-NITRO-SALICYLIDENE- (2-MORPHOLINO)ETHYLIMINE (HL2)

Two azomethynes, namely, derivatives of 5-bromo- and 3-nitrosalicyl aldehydes and 2-morpholinoethylamine ( HL 1 , Z  = Br and HL 2 , Z  = NO 2 ; in HL 1,2 R = CH 2 CH 2 N(CH 2 ) 4 O) are synthesized and analyzed by IR spectroscopy and single crystal X-ray diffraction. A benzenoid (enolimine) tautome...

Full description

Saved in:
Bibliographic Details
Published in:Journal of structural chemistry 2021-03, Vol.62 (3), p.436-442
Main Authors: Sergienko, V. S., Abramenko, V. L., Churakov, A. V., Surazhskaya, M. D.
Format: Article
Language:English
Subjects:
Aldehydes
Atomic
Atomic/Molecular Structure and Spectra
Chemistry
Chemistry and Materials Science
Crystal structure
Crystals
Hydrogen bonds
Infrared spectroscopy
Inorganic Chemistry
Molecular
Nitrogen dioxide
Optical and Plasma Physics
Physical Chemistry
Quinones
Single crystals
Solid State Physics
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two azomethynes, namely, derivatives of 5-bromo- and 3-nitrosalicyl aldehydes and 2-morpholinoethylamine ( HL 1 , Z  = Br and HL 2 , Z  = NO 2 ; in HL 1,2 R = CH 2 CH 2 N(CH 2 ) 4 O) are synthesized and analyzed by IR spectroscopy and single crystal X-ray diffraction. A benzenoid (enolimine) tautomeric form (a hydrogen atom is located at an oxygen atom) occurs in HL 1 . The structure is stabilized by an intramolecular О1–Н1В…N1 hydrogen bond (О–H 0.87(4) Å, H…N 1.83(4) Å, O…N 2.586(4) Å, ОHN angle 143(4)°). The HL 2 molecule crystallizes in the quinoidal (quinone amine) tautomeric form with the intramolecular N1–Н1…O2 hydrogen bond (N–H 0.87(2) Å, H…O 1.99(2) Å, O…N 2.659(2) Å, NHO angle 134(2)°).
ISSN:0022-4766
1573-8779
DOI:10.1134/S0022476621030100