Unexpected hydrogen bonding in the crystal structure of (4-chlorophenyl)propiolic acid. Role of C-H hor ellipsis O hydrogen bonds in determining O-H hor ellipsis O networks

Journal Article · · Chemistry of Materials; (USA)

OSTI ID:6381677

Desiraju, G R; Murty, B N; Radha Kishan, K V ^[1]

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1. Univ. of Hyderabad (India)

There is a very strong tendency for carboxylic acids to form centrosymmetric, hydrogen-bonded dimers in the solid state, and recent studies have attempted to use this dimeric building block in the crystal engineering of molecular solids. However, hydrogen-bonded molecules of (4-chlorophenyl)propiolic acid, p-ClC{sub 6}H{sub 4}C{triple bond}CCO{sub 2}H, do not pack in the crystal according to the predicted dimer motif but, in an unusual manner for this category of molecule, in the catemer arrangement. Crystals of this compound are triclinic, space group P{anti 1}, Z = 2, a = 6.120 (4) {angstrom}, b = 17.323 (13) {angstrom}, c = 3.944 (2) {angstrom}, {alpha} = 90.47 (6){degree}, {beta} = 92.70 (5){degree}, {gamma} = 102.26 (6){degree}, R = 0.065, R{sub w} = 0.071, with 831 nonzero reflections. The catemer arrangement observed in this case might have been anticipated for some other carboxylic acids, but it is unexpected here and could arise due to the inability of the molecules to form C-H{hor ellipsis}O hydrogen bonds.

• OSTI ID: 6381677
• Journal Information: Chemistry of Materials; (USA), Vol. 2:4; ISSN 0897-4756
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
CARBOXYLIC ACIDS
CRYSTAL STRUCTURE
INTERMOLECULAR FORCES
BONDING
DATA ANALYSIS
EXPERIMENTAL DATA
MEASURING INSTRUMENTS
MEASURING METHODS
NONLINEAR OPTICS
DATA
FABRICATION
INFORMATION
JOINING
NUMERICAL DATA
OPTICS
ORGANIC ACIDS
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400201* - Chemical & Physicochemical Properties