Vapor Pressures of Four Methyl Esters of Substituted Benzoic Acids. The Intermolecular Hydrogen Bond OH···O

2016 ◽  
Vol 61 (2) ◽  
pp. 1012-1020 ◽  
Author(s):  
Ana R. R. P. Almeida ◽  
Manuel J. S. Monte
Keyword(s):  
Hydrogen Bond ◽  
Methyl Esters ◽  
Intermolecular Hydrogen Bond ◽  
Benzoic Acids ◽  
Vapor Pressures ◽  
Substituted Benzoic Acids

scholarly journals Role of pK a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

2021 ◽  
Vol 77 (11) ◽  
Author(s):  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bond ◽  
Shape Index ◽  
Benzoic Acids ◽  
Quinoline Ring ◽  
Nitrobenzoic Acid ◽  
Layer Structures ◽  
Acid And Base ◽  
Short Hydrogen Bond ◽  
Substituted Benzoic Acids ◽  
Hydrogen Bonded

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4 −, (I), 4-methylquinoline–2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO4 0.63−, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO4 0.54−, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4 −, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4 −, have been determined at 185–190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, respectively, for compounds (I)–(VI). In the hydrogen-bonded acid–base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)–(VI), π–π stacking interactions between the quinoline ring systems and C—H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)–(VI) through these interactions together with π–π interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N—O...π interaction are present in (I), while a C—H...Cl hydrogen bond and a π–π interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C—H...π interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over d norm and shape index were generated to visualize the weak intermolecular interactions.

Correction. Methyl Esters of Substituted Benzoic Acids

1952 ◽  
Vol 74 (24) ◽  
pp. 6319-6319
Author(s):  
Robert West ◽  
Severo Ornstein ◽  
Donald McKee ◽  
Robert Layzer
Keyword(s):  
Methyl Esters ◽  
Benzoic Acids ◽  
Substituted Benzoic Acids

THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY ULTRAVIOLET LIGHT ABSORPTION: PART III. THE STRENGTH OF THE DIMERIC HYDROGEN BOND IN SUBSTITUTED BENZOIC ACIDS AS A MEASURE OF ELECTRONIC AND STERIC INTERACTIONS

1960 ◽  
Vol 38 (5) ◽  
pp. 728-735 ◽  
Author(s):  
W. F. Forbes ◽  
A. R. Knight ◽  
D. L. Coffen
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Concentration Dependence ◽  
Intramolecular Hydrogen Bond ◽  
Light Absorption ◽  
Benzoic Acids ◽  
Steric Interactions ◽  
Substituted Benzoic Acids ◽  
Intramolecular Hydrogen ◽  
Methoxybenzoic Acid

The strength of the intermolecular (dimeric) hydrogen bond in substituted benzoic acids, as estimated from the observed concentration dependence of the ultraviolet absorption spectra, is found to vary with the nature and the position of the substituent. The effects of a number of substituents on the strength of the dimeric hydrogen bond can be rationalized in terms of the usual electronic and steric interactions. The data indicate that o-methoxybenzoic acid forms a stronger intramolecular hydrogen bond than o-fluorobenzoic acid.

Hydrogen bond in o-phosphorus-substituted benzoic acids

1981 ◽  
Vol 30 (7) ◽  
pp. 1318-1321 ◽  
Author(s):  
E. I. Matrosov ◽  
N. A. Bondarenko ◽  
E. N. Tsvetkov ◽  
M. I. Kabachnik
Keyword(s):  
Hydrogen Bond ◽  
Benzoic Acids ◽  
Substituted Benzoic Acids
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