Intermolecular amide and aldehyde interactions: rotational spectroscopy of the complexes of formaldehyde with 2-azetidinone and formamide

Abstract

The binary intermolecular complexes of amides and formaldehyde can be taken as suitable models to investigate the non-covalent interactions of the peptide with carbonyl group. We herein studied the rotational...

Unveiling the Noncovalent Interactions between Formamide and Heteroaromatics: Microwave Spectroscopy of the Formamide Complexes with Furan and Thiophene

“…The N–H···OC hydrogen bonding interaction between amides is the key type of noncovalent linkage determining the stability of biomacromolecules like proteins and peptides as well as controlling their binding with small molecules, which therefore is indispensable to comprehend the function and activity of these compounds. − Formamide (FM), being the simplest molecule that contains the amide functional group, acts as a preferred model for probing the properties of weak interactions of peptide linkage. − FM has a CO bond and two N–H bonds, which are typical proton acceptors and donors for forming the N–H···OC hydrogen bonding interactions. In this context, model complexes containing FM are intensively investigated, both computationally and experimentally.…”

“…The complexes of FM with water [FM-H 2 O (6) , FM-(H 2 O) 2–3 , , and (FM) 2 -H 2 O] are found mainly linked by N–H···O and O–H···O hydrogen bonds. The complexes of FM with methanol, formic acid, and formaldehyde are also mainly stabilized through N–H···O or O–H···O hydrogen bonds with C–H···O hydrogen bond acting as secondary interactions. The complexes formed by FM with CO 2 , CH 2 F 2 , and CH 3 SCH 3 are composed of O···C and N–H···O interactions, N–H···F and C–H···O interactions, and N–H···S and C–H···O interactions, respectively.…”

Three non-bonding interaction topologies of the thiazole–formaldehyde complex observed by rotational spectroscopy

“…amide N-HÁ Á ÁOQC HB. 11 The important roles of such HBs in determining the conformations of peptides have been recognized long ago, [12][13][14] and then extensively studied. [15][16][17][18][19][20] Nucleophiles such as the lone-pairs of carbonyl oxygen can interact with the p-antibonding orbital (p*) of a carbonyl group along the Bu ¨rgi-Dunitz trajectory.…”