The effect of hydrogen bonding on the bond lengths and angles in the carboxyl group

1979 ◽  
Vol 9 (2) ◽  
pp. 87-105 ◽  
Author(s):  
Mizuhiko Ichikawa
Keyword(s):  
Hydrogen Bonding ◽  
Carboxyl Group ◽  
Bond Lengths

Hydrogen-bonding patterns in the cocrystal 2,4-diamino-6-phenyl-1,3,5-triazine–sorbic acid (1/1)

2007 ◽  
Vol 63 (11) ◽  
pp. o4450-o4451 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Sorbic Acid ◽  
Carboxyl Group ◽  
Amino Group ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Graph Set ◽  
Bonding Patterns

In the title cocrystal, C9H9N5·C6H8O2, the asymmetric unit contains one 2,4-diamino-6-phenyl-1,3,5-triazine molecule and a sorbic acid molecule. The triazine molecules are base-paired [with a graph set of R 2 2(8)] on either side via N—H...N hydrogen bonds, forming a supramolecular ribbon along the c axis. Each triazine molecule interacts with the carboxyl group of a sorbic acid molecule via N—H...O and O—H...N hydrogen bonds, generating R 2 2(8) motifs. The supramolecular ribbons are interlinked by N—H...O hydrogen bonds involving the 2-amino group of the triazine molecules and the carboxyl O atom of the sorbic acid molecule.

Effect of intramolecular hydrogen bonding on the relative acidities of substituted salicylic acids in benzene solution

1967 ◽  
Vol 45 (14) ◽  
pp. 1699-1706 ◽  
Author(s):  
G. E. Dunn ◽  
Thomas L. Penner
Keyword(s):  
Hydrogen Bonding ◽  
Electronic Effect ◽  
Benzene Solution ◽  
Intramolecular Hydrogen Bonding ◽  
Acid Strength ◽  
Carboxyl Group ◽  
Hammett Equation ◽  
Phenolic Group ◽  
Intramolecular Hydrogen ◽  
Salicylic Acids

The relative acidities of fifteen 4- and 5-substituted salicylic acids were determined in benzene solution by potentiometric titration. The potentials at half neutralization (h.n.p.) relative to that of salicylic acid were considered to measure the acidities of the substituted acids relative to the parent acid. These potentials, designated by Δhnp, gave a significantly better correlation with Hammett's sigma constants in an equation of the form proposed by Jaffe, Δhnp = ρ1σ1 + ρ2σ2, than in a simple Hammett equation, Δhnp = ρ1σ1. In these equations the subscripts 1 and 2 refer to the position of a substituent relative to the carboxyl group and to the phenolic group respectively. The value of ρ2/ρ1 was found to be 0.4, indicating that the electronic effect of a substituent on the acid strength via the phenolic hydrogen-bonded path is almost half as large as the direct effect through the carboxyl group. These results, together with the fact that in aqueous solution there is very little if any transmission via the phenolic group, are discussed in terms of intramolecular hydrogen bonding of salicylic acids in benzene and in water.

scholarly journals Hydrogen-bonding to M-O2 and M = O in porphyrin models equipped with an intramolecular carboxyl group.

1993 ◽  
Vol 51 (1-2) ◽  
pp. 288
Author(s):  
C.K. Chang ◽  
Y. Liang ◽  
G. Avilés ◽  
E. Schmidt ◽  
S.-M. Peng
Keyword(s):  
Hydrogen Bonding ◽  
Carboxyl Group

3-(4-Oxocyclohexyl)propionic acid monohydrate: hydrogen bonding in the hydrate of a ζ-keto acid

2007 ◽  
Vol 63 (3) ◽  
pp. o1173-o1175
Author(s):  
Stephanie M. Witko ◽  
Mark Davison ◽  
Hugh W. Thompson ◽  
Roger A. Lalancette
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Carboxyl Group ◽  
Keto Acid ◽  
Carbonyl Groups ◽  
O 178 ◽  
Network Of Hydrogen Bonds

In the title crystal structure, C9H14O3·H2O, the water molecule accepts a hydrogen bond from the carboxyl group [O...O = 2.6004 (13) Å and O—H...O = 163°], while donating hydrogen bonds to the ketone [O...O = 2.8193 (14) Å and O—H...O = 178 (2)°] and the acid carbonyl groups [O...O = 2.8010 (14) Å and O—H...O = 174 (2)°]. This creates a network of hydrogen bonds confined within a continuous flat ribbon two molecules in width and extending in the [101] direction.

scholarly journals Crystal structures ofN′-aminopyridine-2-carboximidamide andN′-{[1-(pyridin-2-yl)ethylidene]amino}pyridine-2-carboximidamide

2017 ◽  
Vol 73 (7) ◽  
pp. 1021-1025
Author(s):  
Francois Eya'ane Meva ◽  
Timothy John Prior ◽  
David John Evans ◽  
Emmanuel Roland Mang
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Dimensional Chain ◽  
Two Dimensional ◽  
One Dimensional ◽  
Bond Lengths ◽  
Hydrogen Bonding Interactions ◽  
Hydrogen Bonding Network

The crystal structures ofN′-aminopyridine-2-carboximidamide (C6H8N4),1, andN′-{[1-(pyridin-2-yl)ethylidene]amino}pyridine-2-carboximidamide (C13H13N5),2, are described. The non-H atoms in compound1are nearly planar (r.m.s. deviation from planarity = 0.0108 Å), while2is twisted about the central N—N bond by 17.8 (2)°. Both molecules are linked by intermolecular N—H...N hydrogen-bonding interactions;1forms a two-dimensional hydrogen-bonding network and for2the network is a one-dimensional chain. The bond lengths of these molecules are similar to those in other literature reports of azine and diimine systems.

scholarly journals Hydrogen-bonding patterns in 2-amino-4,6-dimethoxypyrimidine–4-aminobenzoic acid (1/1)

2006 ◽  
Vol 62 (7) ◽  
pp. o2976-o2978 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Carboxyl Group ◽  
Acid Molecule ◽  
Aminobenzoic Acid ◽  
Graph Set ◽  
Supramolecular Chain ◽  
Bonding Patterns ◽  
Hydrogen Bonded

In the title cocrystal, C6H9N3O2·C7H7NO2, the 2-amino-4,6-dimethoxypyrimidine molecule interacts with the carboxyl group of the 4-aminobenzoic acid molecule through N—H...O and O—H...N hydrogen bonds, forming a cyclic hydrogen-bonded motif [R 2 2(8)]. This motif further self-organizes through N—H...O hydrogen bonds to generate an array of six hydrogen bonds with the rings having the graph-set notation R 2 3(6), R 2 2(8), R 4 2(8), R 2 2(8) and R 2 3(6). The 4-aminobenzoic acid molecules self-assemble via N—H...O hydrogen bonds to form a supramolecular chain along the c axis.

scholarly journals Metal Complex Geometries in Small-Molecule Crystals

1998 ◽  
Vol 54 (6) ◽  
pp. 1194-1198 ◽  
Author(s):  
A. Guy Orpen
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Metal Complex ◽  
Small Molecule ◽  
Structure Determination ◽  
Complex Geometries ◽  
Bond Lengths ◽  
Structural Database ◽  
Metal Ligand ◽  
Ligand Bond

The origins, scope and utility of compilations of metal–ligand and intraligand bond lengths based on the Cambridge Structural Database are discussed. The limitations on the apparent uncertainty of metal–ligand bond lengths derived from crystallographic data and recent evidence of metal-assisted hydrogen bonding involving ligands are reviewed in the light of the transferability of bond-length values from one crystal structure determination.

Erdalkaliquadratate, I BaC4O4 · 3H2O / Alkaline-earth Squarates, I BaC4O4 · 3H2O

1986 ◽  
Vol 41 (12) ◽  
pp. 1485-1489 ◽  
Author(s):  
Christian Robl ◽  
Armin Weiss
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Silica Gel ◽  
Alkaline Earth ◽  
Three Dimensional ◽  
Water Molecules ◽  
Bond Lengths ◽  
Resonance Stabilization ◽  
Aqueous Silica

Abstract BaC4O4-3H2O was prepared by crystallization in aqueous silica gel. The crystal structure is a complicated three-dimensional framework. Ba2+ has CN 8+1. It is surrounded by 5 water molecules and 4 Osquarate atoms (Ba-O distances from 271.1 to 324.2 pm). The squarate dianion is almost planar and shows C -C and C-O bond lengths indicating the existence of resonance stabilization, although one Osquarate atom is not connected to Ba2+ at all. Short water-Osquarate distances hint to strong hydrogen bonding which obviously plays an important part in this structure.

Four (2,2′-bipyridyl)(ferrocenyl)boronium derivatives

2015 ◽  
Vol 71 (1) ◽  
pp. 26-31 ◽  
Author(s):  
Jan W. Bats ◽  
Kuangbiao Ma ◽  
Hans-Wolfram Lerner
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Tetrahedral Coordination ◽  
Asymmetric Unit ◽  
Bond Lengths ◽  
Distorted Tetrahedral Coordination

Crystal structures are reported for four (2,2′-bipyridyl)(ferrocenyl)boronium derivatives, namely (2,2′-bipyridyl)(ethenyl)(ferrocenyl)boronium hexafluoridophosphate, [Fe(C5H5)(C17H15BN2)]PF6, (Ib), (2,2′-bipyridyl)(tert-butylamino)(ferrocenyl)boronium bromide, [Fe(C5H5)(C19H22BN3)]Br, (IIa), (2,2′-bipyridyl)(ferrocenyl)(4-methoxyphenylamino)boronium hexafluoridophosphate acetonitrile hemisolvate, [Fe(C5H5)(C22H20BN3O)]PF6·0.5CH3CN, (IIIb), and 1,1′-bis[(2,2′-bipyridyl)(cyanomethyl)boronium]ferrocene bis(hexafluoridophosphate), [Fe(C17H14BN3)2](PF6)2, (IVb). The asymmetric unit of (IIIb) contains two independent cations with very similar conformations. The B atom has a distorted tetrahedral coordination in all four structures. The cyclopentadienyl rings of (Ib), (IIa) and (IIIb) are approximately eclipsed, while a bisecting conformation is found for (IVb). The N—H groups of (IIa) and (IIIb) are shielded by the ferrocenyl andtert-butyl or phenyl groups and are therefore not involved in hydrogen bonding. The B—N(amine) bond lengths are shortened by delocalization of π-electrons. In the cations with an amine substituent at boron, the B—N(bipyridyl) bonds are 0.035 (3) Å longer than in the cations with a methylene C atom bonded to boron. A similar lengthening of the B—N(bipyridyl) bonds is found in a survey of related cations with an oxy group attached to the B atom.

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