Proton transfer in hydrogen bonded systems

1960 ◽  
Vol 257 (1288) ◽  
pp. 98-108 ◽  
Keyword(s):  
Hydrogen Bond ◽  
Absorption Band ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Direct Result ◽  
Isotopic Substitution ◽  
Association Energy ◽  
Hydrogen Bonded Systems ◽  
Hydrogen Bonded

Evidence is presented that proton transfer occurs in certain special types of hydrogen bond and that as a direct result the association energy is increased. It is probable that this effect is also responsible for a t least a part of the broadening of the v XH absorption band. In support of this, a number of com pounds are described in which the hydrogen bonds are weakened by isotopic substitution. The implications of these findings are discussed.

scholarly journals Di-μ-chlorido-bis[(2,2′-bipyridine-5,5′-dicarboxylic acid-κ2N,N′)chloridocopper(II)] dimethylformamide tetrasolvate

2013 ◽  
Vol 69 (2) ◽  
pp. m73-m74 ◽  
Author(s):  
Sigurd Øien ◽  
David Stephen Wragg ◽  
Karl Petter Lillerud ◽  
Mats Tilset
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Cooh Group ◽  
Stacking Interactions ◽  
Coordination Geometry ◽  
Complex Molecules ◽  
Centroid Distance ◽  
Solvent Molecules ◽  
Hydrogen Bonded

In the title compound, [Cu2Cl4(C12H8N2O4)2]·4C3H7NO, which contains a chloride-bridged centrosymmetric CuIIdimer, the CuIIatom is in a distorted square-pyramidal 4 + 1 coordination geometry defined by the N atoms of the chelating 2,2′-bipyridine ligand, a terminal chloride and two bridging chloride ligands. Of the two independent dimethylformamide molecules, one is hydrogen bonded to a single –COOH group, while one links two adjacent –COOH groupsviaa strong accepted O—H...O and a weak donated C(O)—H...O hydrogen bond. Two of these last molecules and the two –COOH groups form a centrosymmetric hydrogen-bonded ring in which the CH=O and the –COOH groups by disorder adopt two alternate orientations in a 0.44:0.56 ratio. These hydrogen bonds link the CuIIcomplex molecules and the dimethylformamide solvent molecules into infinite chains along [-111]. Slipped π–π stacking interactions between two centrosymmetric pyridine rings (centroid–centroid distance = 3.63 Å) contribute to the coherence of the structure along [0-11].

Damaging Intermolecular Energy and Proton Transfer Processes in Alpha-Particle-Irradiated Hydrogen-Bonded Systems

2018 ◽  
Vol 130 (52) ◽  
pp. 17269-17273 ◽  
Author(s):  
Shenyue Xu ◽  
Dalong Guo ◽  
Xinwen Ma ◽  
Xiaolong Zhu ◽  
Wentian Feng ◽  
...  
Keyword(s):  
Proton Transfer ◽  
Alpha Particle ◽  
Transfer Processes ◽  
Intermolecular Energy ◽  
Hydrogen Bonded Systems ◽  
Hydrogen Bonded

scholarly journals Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-aminophenylarsonate tetrahydrate

2016 ◽  
Vol 72 (5) ◽  
pp. 751-755 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Network Structure ◽  
Three Dimensional ◽  
Water Molecules ◽  
Arsanilic Acid ◽  
Dimensional Network

In the structure of the brucinium salt of 4-aminophenylarsonic acid (p-arsanilic acid), systematically 2,3-dimethoxy-10-oxostrychnidinium 4-aminophenylarsonate tetrahydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water molecules of solvation are accommodated between the layers and are linked to them through a primary cation N—H...O(anion) hydrogen bond, as well as through water O—H...O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure.

Polysulfonylamine, CLXXXIX [1]. Weitere Beispiele für die O-Protonierung von Harnstoffen mit Di(organosulfonyl)aminen: Bildung und Kristallstrukturen von 1,1-Dimethyluroniumdi( 4-fluorbenzolsulfonyl)amid und Di(1-methylharnstoff)- hydrogen(I)-di(4-fluorbenzolsulfonyl)amid/ Polysulfonylamines, CLXXXIX. Additional Examples of the O-Protonation of Ureas by Di(organosulfonyl)amines: Formation and Crystal Structures of 1,1-Dimethyluronium Di(4-fluorobenzenesulfonyl)amide and Di(1-methylurea)hydrogen(I)Di(4-fluorobenzenesulfonyl) amide

2010 ◽  
Vol 65 (11) ◽  
pp. 1363-1371 ◽  
Author(s):  
Christoph Wölper ◽  
Alejandra Rodríguez-Gimeno ◽  
Katherine Chulvi Iborra ◽  
Peter G. Jones ◽  
Armand Blaschette
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Petroleum Ether ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
One Dimensional ◽  
Bond Lengths ◽  
Ionic Compounds ◽  
Specific Elongation

Co-crystallization of N-methyl-substituted ureas with di(organosulfonyl)amines, (RSO2)2NH, leads unpredictably to either molecular co-crystals or, via proton transfer, to uronium salts. As a sequel to former reports, this communication describes the formation and the crystal structures of the new ionic compounds 1,1-dimethyluronium di(4-fluorobenzenesulfonyl)amide (1, monoclinic, space group P21/c, Z´ = 1) and di(1-methylurea)hydrogen(I) di(4-fluorobenzenesulfonyl)amide (2, triclinic, P1̄, Z´ = 1); both salts were obtained from dichloromethane/petroleum ether. In the structure of 2, the urea moieties of the cationic homoconjugate are connected by a very short [O-H· · ·O]+ hydrogen bond [d(O· · ·O) = 244.6(2) pm, θ (O-H· · ·O)≈170°, bridging H atom asymmetrically disordered over two positions]. The O-protonation induces a specific elongation of the C-O bond lengths to 131.2(2) pm in 1 or 129.5(2) and 127.4(2) pm in 2, as compared to literature data of ca. 126 pm for the unprotonated ureas. Both crystal structures are dominated by conventional two- and threecentre hydrogen bonds, which involve the OH and all NH donors and give rise to one-dimensional cation-anion arrays. In particular, the ionic entities of 1 are alternatingly associated into simple chains propagated by glide-plane operations parallel to the c axis, whereas the donor-richer structure of 2 displays inversion symmetric dimers of formula units, which are further hydrogen-bonded into strands propagated by translation parallel to the a axis.

Two polymorphs and the diethylammonium salt of the barbiturate eldoral

2012 ◽  
Vol 68 (2) ◽  
pp. o65-o70 ◽  
Author(s):  
Thomas Gelbrich ◽  
Denise Rossi ◽  
Ulrich J. Griesser
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Barbituric Acid ◽  
Layer Structure ◽  
Chain Structure ◽  
Hydrogen Bond Acceptor ◽  
Layer Structures ◽  
A Chain ◽  
Derivatives Of ◽  
Hydrogen Bonded

Polymorph (Ia) of eldoral [5-ethyl-5-(piperidin-1-yl)barbituric acid or 5-ethyl-5-(piperidin-1-yl)-1,3-diazinane-2,4,6-trione], C11H17N3O3, displays a hydrogen-bonded layer structure parallel to (100). The piperidine N atom and the barbiturate carbonyl group in the 2-position are utilized in N—H...N and N—H...O=C hydrogen bonds, respectively. The structure of polymorph (Ib) contains pseudosymmetry elements. The two independent molecules of (Ib) are connectedviaN—H...O=C(4/6-position) and N—H...N(piperidine) hydrogen bonds to give a chain structure in the [100] direction. The hydrogen-bonded layers, parallel to (010), formed in the salt diethylammonium 5-ethyl-5-(piperidin-1-yl)barbiturate [or diethylammonium 5-ethyl-2,4,6-trioxo-5-(piperidin-1-yl)-1,3-diazinan-1-ide], C4H12N+·C11H16N3O3−, (II), closely resemble the corresponding hydrogen-bonded structure in polymorph (Ia). Like many other 5,5-disubstituted derivatives of barbituric acid, polymorphs (Ia) and (Ib) contain theR22(8) N—H...O=C hydrogen-bond motif. However, the overall hydrogen-bonded chain and layer structures of (Ia) and (Ib) are unique because of the involvement of the hydrogen-bond acceptor function in the piperidine group.

Two methyl 3-(1H-pyrazol-4-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylates form different hydrogen-bonded sheets

2013 ◽  
Vol 69 (8) ◽  
pp. 915-919
Author(s):  
Jairo Quiroga ◽  
Jaime Gálvez ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Hydrogen Bonded

In the molecules of both methyl (1RS,3SR,3aRS,6aSR)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate, C25H24N4O4, (I), and methyl (1RS,3SR,3aRS,6aSR)-5-(4-chlorophenyl)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate, C25H23ClN4O4, (II), the two rings of the pyrrolopyrrole fragment are both nonplanar, with conformations close to half-chair forms. The overall conformations of the molecules of (I) and (II) are very similar, apart from the orientation of the ester function. The molecules of (I) are linked into sheets by a combination of an N—H...π(pyrrole) hydrogen bond and three independent C—H...O hydrogen bonds. The molecules of (II) are also linked into sheets, which are generated by a combination of an N—H...N hydrogen bond and two independent C—H...O hydrogen bonds, weakly augmented by a C—H...π(arene) hydrogen bond.

scholarly journals (2E)-3-(6-Methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one and its cyclocondensation product with guanidine, (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate: two types of hydrogen-bonded sheet

2014 ◽  
Vol 70 (11) ◽  
pp. 1011-1016 ◽  
Author(s):  
Prakash S. Nayak ◽  
Badiadka Narayana ◽  
Hemmige S. Yathirajan ◽  
Eric C. Hosten ◽  
Richard Betz ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Dihedral Angles ◽  
Form Complex ◽  
Molecular Components ◽  
Hydrogen Bonded

The structures of a chalcone and of its cyclocondensation product with guanidine are reported. In (2E)-3-(6-methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one, C19H15NO2, (I), the planes of the pyridine and naphthalene units make dihedral angles with that of the central spacer unit of 23.61 (13) and 23.57 (15)°, respectively, and a dihedral angle of 47.24 (9)° with each other. The molecules of (I) are linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds. In the cyclocondensation product (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate, C20H18N4O·H2O, (II), the dihydropyrimidine ring adopts a conformation best described as a shallow boat. The molecular components are linked by two N—H...O hydrogen bonds, two O—H...N hydrogen bonds and one N—H...N hydrogen bond to form complex sheets, with the methoxynaphthalene interdigitated between inversion-related pairs of sheets.

Sign in / Sign up

Export Citation Format

Share Document