FTIR study of H-bonds cooperativity in complexes of 1,2-dihydroxybenzene with proton acceptors in aprotic solvents: influence of the intramolecular hydrogen bond.
FTIR spectroscopic study of hydrogen bonding of 1,2-dihydroxybenzene (catechol) with proton acceptors has been carried out. The influence of intramolecular and intermolecular hydrogen bonds on the strengths of each other in complexes of 1,2-dihydroxybenzene with various proton acceptors has been analyzed. It was shown that intramolecular hydrogen bond is strengthened when 1,2-dihydroxybenzene interacts with bases (ethers, amines, nitriles, etc.) in inert solvents. The contribution of the cooperativity of intramolecular hydrogen bonds in the frequency of stretching vibrations of O-H groups linearly depends on the proton acceptor ability of the bases. The solvent effect on hydrogen bond cooperativity in 1,2-dihydroxybenzene-base complexes has been studied. The approach to determine the influence of cooperative effects on the formation of intermolecular complexes with 1,2-dihydroxybenzene is proposed. It was shown that the strength of intramolecular hydrogen bonds in the complexes of 1,2-dihydroxybenzene with bases due to cooperativity of interactions increases by 30-70%, and the strength of intermolecular hydrogen bond by 7-22%.
Varfolomeev
Mikhail A
MA
Chemical Institute, Kazan State University, Kremlevskaya 18, Kazan 420008, Russia. vma.ksu@gmail.com
Abaidullina
Dilyara I
DI
Gainutdinova
Aliya Z
AZ
Solomonov
Boris N
BN
D001667:Binding, Competitive / Q000502:physiology; D002396:Catechols / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D046911:Macromolecular Substances / Q000737:chemistry*; D008954:Models, Biological; D008958:Models, Molecular; D011522:Protons; D012997:Solvents / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods
D002396:Catechols; D046911:Macromolecular Substances; D011522:Protons; D012997:Solvents; D006859:Hydrogen; C034221:catechol