Hydrogen Bonding Modulates the Selectivity of Enzymatic Oxidation by P450: Chameleon Oxidant Behavior by Compound I The research was supported in parts by the Israel Science Foundation (ISF), the German Israeli Binational Foundation (GIF), and by the Ministry of Science, Culture, and Sports. F.O. thanks the European community for a Marie Curie Fellowship.

2002 ◽  
Vol 41 (11) ◽  
pp. 1947 ◽  
Author(s):  
Samuël P. de Visser ◽  
François Ogliaro ◽  
Pankaz K. Sharma ◽  
Sason Shaik
Keyword(s):  
Hydrogen Bonding ◽  
European Community ◽  
Enzymatic Oxidation ◽  
Marie Curie ◽  
Compound I ◽  
Science Culture ◽  
Curie Fellowship

N-[2-(Pyridin-2-yl)ethyl]-derivatives of methane-, benzene- and toluenesulfonamide: prospective ligands for metal coordination

2013 ◽  
Vol 69 (11) ◽  
pp. 1397-1401 ◽  
Author(s):  
Danielle L. Jacobs ◽  
Benny C. Chan ◽  
Abby R. O'Connor
Keyword(s):  
Hydrogen Bonding ◽  
Dihedral Angles ◽  
Compound I ◽  
Torsion Angles ◽  
Methyl Group ◽  
A Value ◽  
Π Stacking ◽  
Linear Chains ◽  
Centroid Distance ◽  
Derivatives Of

The molecular and supramolecular structures are reported ofN-[2-(pyridin-2-yl)ethyl]methanesulfonamide, C8H12N2O2S, (I),N-[2-(pyridin-2-yl)ethyl]benzenesulfonamide, C13H14N2O2S, (II), andN-[2-(pyridin-2-yl)ethyl]toluenesulfonamide, C14H16N2O2S, (III). Although (II) and (III) are almost structurally identical, the N(amide)—C(ethyl)—C(ethyl)—C(pyridinyl) torsion angles for (I) and (II) are more closely comparable, with magnitudes of 175.37 (15)° for (I) and 169.04 (19)° for (II). This angle decreases dramatically with an additional methyl group in theparaposition of the sulfonamide substituent, resulting in a value of 62.9 (2)° for (III). In each of the three compounds there is an N—H...N hydrogen bond between the sulfonamide of one molecule and the pyridine N atom of a neighbor. Compound (I) forms hydrogen-bonded dimers, (II) uses its hydrogen bonding to connect supramolecular layers, and the hydrogen bonding of (III) connects linear chains to form layers. For arene-substituted (II) and (III), the different conformations afforded by the variable dihedral angles promote intermolecular π–π stacking in the benzene-substituted structure (II), but distorted intramolecular T-shaped π-stacking in the toluene-substituted structure (III), with a centroid-to-centroid distance of 4.9296 (10) Å.

[Ni(cyclam)(OCOR)2], a finite molecular complex: hydrogen-bonded supramolecular aggregation in one, two and three dimensions, and coordination polymers in one and two dimensions

2001 ◽  
Vol 58 (1) ◽  
pp. 78-93 ◽  
Author(s):  
Choudhury M. Zakaria ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonding ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Two Dimensions ◽  
Three Dimensions ◽  
Two Dimensional ◽  
Compound I ◽  
Supramolecular Aggregation ◽  
Linear Coordination

In the complexes [Ni(cyclam)(OCOR)2] (cyclam = 1,4,8,11-tetraazacyclotetradecane), where (RCOO)− is 2-naphtho-ate [bis-(2-naphthoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (I), monoclinic P21/c, Z′ = 0.5], 3,5-dinitrobenzoate [bis-(3,5-dinitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (II), triclinic P\bar 1, Z′ = 0.5], 4-nitrobenzoate [bis-(4-nitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (III), monoclinic P21/n, Z′ = 0.5], 3-hydroxybenzoate [bis-(3-hydroxybenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (IV), monoclinic P21/c, Z′ = 0.5] and 4-aminobenzo-ate [bis-(4-aminobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (V), monoclinic C2/c, Z′ = 0.5], the Ni lies on a centre of inversion with monodentate carboxylato ligands occupying trans sites. Compound (I) consists of isolated molecules. In (II) and (III), N—H...O hydrogen bonds link the complexes into chains. Compounds (IV) and (III) form two- and three-dimensional structures generated entirely by hard hydrogen bonds. The 5-hydroxyisophthalate(2−) anion forms a hydrated complex, [Ni(cyclam)(5-hydroxyisophthalate)(H2O)]·4H2O {[aqua-(5-hydroxyisophthalato)-1,4,8,11-tetraazacyclotetradecanenickel(II)] tetrahydrate, (VI), monoclinic Cc, Z′ = 1}, in which the monodentate carboxylato ligand and a water molecule occupy trans sites at Ni: extensive hydrogen bonding links the molecular aggregates into a three-dimensional framework. The terephthalate(2−) anion forms a hydrated linear coordination polymer {catena-poly[terephthalato-1,4,8,11-tetraazacyclotetradecanenickel(II)] monohydrate, (VII), monoclinic C2/c, Z′ = 0.5}. In 1,2,4,5-benzenecarboxylate tris[1,4,8,11-tetraazacyclotetradecanenickel(II)] diperchlorate hydrate (VIII), [Ni(cyclam)]3·[1,2,4,5-benzenetetracarboxylate(4−)]·[ClO4]2·-[H2O]3, there are two distinct Ni sites: [Ni(cyclam)]2+ and centrosymmetric [C10H2O8]4− units form a two-dimensional coordination polymer, whose sheets are linked by centrosymmetric [Ni(cyclam)(H2O)2]2+ cations.

scholarly journals Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C—N...π interactions

2018 ◽  
Vol 74 (12) ◽  
pp. 1717-1726
Author(s):  
Abderezak Addala ◽  
Zouaoui Setifi ◽  
Yukio Morimoto ◽  
Beñat Artetxe ◽  
Takashi Matsumoto ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Compound I ◽  
Π Interactions ◽  
Chain Compounds ◽  
Compound Ii ◽  
Ionic Components

Structures are reported for six closely related salts of tris(bipyridyl)iron(II) cations, namely tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-methoxypropenide) 0.776-hydrate, [Fe(C10H8N2)3](C8H3N4O)2.0.776H2O, (I), tris(2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(propylsulfanyl)propenide perchlorate, [Fe(C10H8N2)3](C10H7N4S)(ClO4), (II), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-methoxypropenide tetrafluoridoborate ethanol 0.926-solvate, [Fe(C12H12N2)3](C8H3N4O)(BF4).0.926C2H2O, (III), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-ethoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4O)(BF4), (IV), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(ethylsufanyl)propenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4S)(BF4), (V), and tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-propoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C10H7N4O)(BF4), (VI). In compound (I), one of the anions is disordered over two sets of atomic sites with equal occupancies while, in the second anion, just one of the C(CN)2 units is disordered, again over two sets of atomic sites with equal occupancies: the anionic components are linked by multiple C—H...N hydrogen bonds to form a three-dimensional framework. In compound (II), the polynitrile anion is disordered over two sets of atomic sites with occupancies in the approximate ratio 3:1, while the perchlorate anion is disordered over three sets of atomic sites: there are C—N...π interactions between the cations and the polynitrile anion. The polynitrile anion in compound (III) is fully ordered, but the tetrafluoridoborate anion is disordered over two sets of atomic sites with occupancies 0.671 (4) and 0.329 (4): the cations and the tetrafluoridoborate anions are linked by C—H...F interactions to form an interrupted chain. Compounds (IV) and (V) are isostructural and all of the ionic components are fully ordered in both of them: the cations and tetrafluoridoborate anions are linked into C 2 2(12) chains. The polynitrile anion in compound (VI) is disordered over two sets of atomic sites with approximately equal occupancies, and here the chains formed by the cations and the tetrafluoridoborate anions are of the C 2 2(13) type.

scholarly journals Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated fromHibiscus sabdariffa(Malvaceae)

2017 ◽  
Vol 73 (9) ◽  
pp. 1368-1371 ◽  
Author(s):  
Ahmed M. Zheoat ◽  
Alexander I. Gray ◽  
John O. Igoli ◽  
Alan R. Kennedy ◽  
Valerie A. Ferro
Keyword(s):  
Hydrogen Bonding ◽  
Dimethyl Sulfoxide ◽  
Dimethyl Ester ◽  
Biologically Active ◽  
Hibiscus Sabdariffa ◽  
Compound I ◽  
One Dimensional ◽  
Acid Dimethyl Ester ◽  
Solvent Molecules ◽  
Compound Ii

The biologically active title compounds have been isolated fromHibiscus sabdariffaplants, hibiscus acid as a dimethyl sulfoxide monosolvate [systematic name: (2S,3R)-3-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylic acid dimethyl sulfoxide monosolvate], C6H6O7·C2H6OS, (I), and hibiscus acid dimethyl ester [systematic name: dimethyl (2S,3R)-3-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylate], C8H10O7, (II). Compound (I) forms a layered structure with alternating layers of lactone and solvent molecules, that include a two-dimensional hydrogen-bonding construct. Compound (II) has two crystallographically independent and conformationally similar molecules per asymmetric unit and forms a one-dimensional hydrogen-bonding construct. The known absolute configuration for both compounds has been confirmed.

Medium Polarization and Hydrogen Bonding Effects on Compound I of Cytochrome P450:  What Kind of a Radical Is It Really?

2000 ◽  
Vol 122 (51) ◽  
pp. 12892-12893 ◽  
Author(s):  
François Ogliaro ◽  
Shimrit Cohen ◽  
Samuël P. de Visser ◽  
Sason Shaik
Keyword(s):  
Hydrogen Bonding ◽  
Cytochrome P450 ◽  
Compound I

scholarly journals Structural characterization of hydrogen bonding for antipyrine derivatives: Single-crystal X-ray diffraction and theoretical studies

2021 ◽  
Vol 16 (2) ◽  
pp. 113-137
Author(s):  
N. S. Rukk ◽  
R. S. Shamsiev ◽  
D. V. Albov ◽  
S. N. Mudretsova
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Electron Density ◽  
Bond Formation ◽  
Intermolecular Hydrogen Bond ◽  
X Ray Diffraction ◽  
Compound I ◽  
Hydrogen Bond Formation ◽  
Compound Ii

Objectives. The paper is devoted to the crystal structure characterization of 5-methyl-2-phenyl4H-pyrazol-3-one (compound I) and 2-(4-chlorophenyl)-5-methyl-4H-pyrazol-3-one (compound II).Methods. Single-crystal X-ray diffraction studies and theoretical calculations: Density functional theory and quantum theory of atoms in molecules.Results. In the solid state, the crystal structure of compound I is characterized by the alternation of OH and NH tautomers connected via O–H---O and N–H---N hydrogen bonds. For compound II, the existence of chains built from the NH monomers via hydrogen bonding can be explained by the peculiarities of cooperative effects. In the framework of quantum theory of atoms in molecules, the following topological characteristics are calculated for all dimers: electron density, Laplacian of electron density, density of kinetic, potential, and total energy in the critical point of the intermolecular hydrogen bond. It is concluded that the hydrogen bond in dimers 1–4, 7 (compound I), and 8–11 (compound II) can be assigned to the intermediate (between covalent and dispersion types) interaction owing to hydrogen bond formation with the participation of electronegative oxygen- (and/or nitrogen-) atoms, whereas H-bond in dimers 5 and 6 (compound I) can be attributed to the dispersion one (no hydrogen bond formation or weak H-bond formation), and it represents the weak interaction, being in agreement with length for intermolecular hydrogen bond in dimers. The electron density and total energy density values demonstrate that the strongest intermolecular H-bonds take place in dimers 1 (OH---O), 4 (OH---O), 7 (OH---N), 8 (OH---O), 9 (NH---N), and 11 (OH---N). The results obtained for compounds I and II are compared with data for antipyrine (1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one; compound III)Conclusions. An important role of intermolecular hydrogen bonding in the crystal packing, molecule association and self-organization via dimer- or more extended species formation has been demonstrated. 

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