ESR Evidence for Proton Tunneling from a Positive Hole through Intermolecular Hydrogen Bond in Irradiated Single Crystals of Carboxylic Acids

In this work, using carboxyl-modified Fe3O4 nanoparticles as a photothermal agent, combining the chemical amide bond and intermolecular hydrogen bond crosslinking force, a photothermal hydrogel with enhanced mechanical properties was...

Download Full-text

Configurational and conformational studies on condensation products of biogenic amines with 2,5-anhydro-D-mannose

Canadian Journal of Chemistry ◽

10.1139/v85-483 ◽

1985 ◽

Vol 63 (11) ◽

pp. 2915-2921 ◽

Cited By ~ 7

Author(s):

Ian M. Piper ◽

David B. MacLean ◽

Romolo Faggiani ◽

Colin J. L. Lock ◽

Walter A. Szarek

Keyword(s):

Hydrogen Bond ◽

Intermolecular Hydrogen Bond ◽

Direct Methods ◽

Conformational Studies ◽

X Ray ◽

X Ray Crystallography ◽

H Nmr ◽

Twist Conformation ◽

Cell Dimensions ◽

Internal Hydrogen Bond

The products of a Pictet–Spengler condensation of tryptamine and of histamine with 2,5-anhydro-D-mannose have been studied by X-ray crystallography to establish their absolute configuration. 1(S)-(α-D-Arabinofuranosyl)-1,2,3,4-tetrahydro-β-carboline (1), C16H20N20O4, is monoclinic, P21 (No. 4), with cell dimensions a = 13.091(4), b = 5.365(1), c = 11.323(3) Å, β = 115.78(2)°, and Z = 2. 4-(α-D-Arabinofuranosyl)imidazo[4,5-c]-4,5,6,7-tetrahydropyridine (3), C11H17N3O4, is orthorhombic, P212121 (No. 19), with cell dimensions a = 8.118(2), b = 13.715(4), c = 10.963(3) Å, and Z = 4. The structures were determined by direct methods and refined to R1 = 0.0514, R2 = 0.0642 for 3210 reflections in the case of 1, and to R1 = 0.0312, R2 = 0.0335 for 1569 reflections in the case of 3. Bond lengths and angles within both molecules are normal and agree well with those observed in related structures. In 3 the base and sugar adopt a syn arrangement, which is maintained by an internal hydrogen bond between O(2′) and N(3). The sugar adopts a normal 2T3 twist conformation. The sugar has the opposite anti arrangement in the β-carboline 1 and the conformation of the sugar is unusual; it is close to an envelope conformation with O(4′) being the atom out of the plane. This conformation is caused by a strong intermolecular hydrogen bond from O(5′) in a symmetry-related molecule to O(4′). Both compounds are held together in the crystal by extensive hydrogen-bonding networks. The conformations of the compounds in solution have been investigated by 1H nmr spectroscopy, and the results obtained were compared with those obtained by X-ray crystallography for 1 and 3.

Download Full-text

Crystal Structures of the Salts of Chiral Primary Amines with Achiral Carboxylic Acids: Recognition of the Commonly-Occurring Supramolecular Assemblies of Hydrogen-Bond Networks and Their Role in the Formation of Conglomerates

Journal of the American Chemical Society ◽

10.1021/ja9539960 ◽

1996 ◽

Vol 118 (14) ◽

pp. 3441-3449 ◽

Cited By ~ 138

Author(s):

Kazushi Kinbara ◽

Yukihiko Hashimoto ◽

Makoto Sukegawa ◽

Hiroyuki Nohira ◽

Kazuhiko Saigo

Keyword(s):

Hydrogen Bond ◽

Crystal Structures ◽

Carboxylic Acids ◽

Supramolecular Assemblies ◽

Primary Amines ◽

Hydrogen Bond Networks

Download Full-text

Intermolecular Hydrogen Bond Plays a Determining Role in Product Selection of Surface Confined Schiff-base Reaction

Chemical Communications ◽

10.1039/d1cc01801a ◽

2021 ◽

Author(s):

Huamei Chen ◽

Guangyuan Feng ◽

Qiu Liang ◽

Enbing Zhang ◽

Yongtao Shen ◽

...

Keyword(s):

Hydrogen Bond ◽

Schiff Base ◽

Hydrogen Bonds ◽

Relative Abundance ◽

Intermolecular Hydrogen Bond ◽

Intermolecular Hydrogen Bonds ◽

Product Selection ◽

Selection Of

Herein, we illustrate how the cooperation of intermolecular hydrogen bonds and conformation flexibility leads to the formation of diverse complex covalent nanostructures on the surface, while the relative abundance of...

Download Full-text

Theoretical Verification of Intermolecular Hydrogen Bond Induced Thermally Activated Delayed Fluorescence in SOBF-Ome

Chinese Physics B ◽

10.1088/1674-1056/ac1b91 ◽

2021 ◽

Author(s):

Mu-Zhen Li ◽

Fei-Yan Li ◽

Qun Zhang ◽

Kai Zhang ◽

Yu-Zhi Song ◽

...

Keyword(s):

Hydrogen Bond ◽

Intermolecular Hydrogen Bond ◽

Delayed Fluorescence ◽

Thermally Activated Delayed Fluorescence ◽

Thermally Activated

Download Full-text

Molecular Structures of Ten Ionic Hydrogen Bond-mediated Anhydrous tert-butylammonium Salts From Different Carboxylic Acids

Journal of Molecular Structure ◽

10.1016/j.molstruc.2021.131917 ◽

2021 ◽

pp. 131917

Author(s):

Xuejuan Yang ◽

Yanhong Zhu ◽

Xinlei Chen ◽

Xingjun Gao ◽

Shouwen Jin ◽

...

Keyword(s):

Hydrogen Bond ◽

Carboxylic Acids ◽

Molecular Structures

Download Full-text

A structural study of (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1,3,5-triphenylcyclohexan-1-ol chloroform hemisolvate and (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1-phenyl-3,5-bis(2-methoxyphenyl)cyclohexan-1-ol

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229615009857 ◽

2015 ◽

Vol 71 (6) ◽

pp. 491-498 ◽

Cited By ~ 2

Author(s):

Mikhail E. Minyaev ◽

Dmitrii M. Roitershtein ◽

Ilya E. Nifant'ev ◽

Ivan V. Ananyev ◽

Tatyana V. Minyaeva ◽

...

Keyword(s):

Crystal Structure ◽

Hydrogen Bond ◽

Single Crystals ◽

Structural Study ◽

Chair Conformation ◽

Cyclohexane Ring ◽

Nmr Studies ◽

Acta Cryst

(1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol or (4-hydroxy-2,4,6-triphenylcyclohexane-1,3-diyl)bis(phenylmethanone), C38H32O3, (1), is formed as a by-product in the NaOH-catalyzed synthesis of 1,3,5-triphenylpentane-1,5-dione from acetophenone and benzaldehyde. Single crystals of the chloroform hemisolvate, C38H32O3·0.5CHCl3, were grown from chloroform. The structure has triclinic (P-1) symmetry. One diastereomer [as a pair of (1RS,2SR,3RS,4SR,5RS)-enantiomers] of (1) has been found in the crystal structure and confirmed by NMR studies. The dichoromethane hemisolvate has been reported previously [Zhanget al.(2007).Acta Cryst.E63, o4652]. (1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-3,5-bis(2-methoxyphenyl)-1-phenylcyclohexan-1-ol or [4-hydroxy-2,6-bis(2-methoxyphenyl)-4-phenylcyclohexane-1,3-diyl]bis(phenylmethanone), C40H36O5, (2), is also formed as a by-product, under the same conditions, from acetophenone and 2-methoxybenzaldehyde. Crystals of (2) have been grown from chloroform. The structure has orthorhombic (Pca21) symmetry. A diastereomer of (2) possesses the same configuration as (1). In both structures, the cyclohexane ring adopts a chair conformation with all bulky groups (benzoyl, phenyl and 2-methoxyphenyl) in equatorial positions. The molecules of (1) and (2) both display one intramolecular O—H...O hydrogen bond.

Download Full-text

Redshift or Adduct Stabilization—A Computational Study of Hydrogen Bonding in Adducts of Protonated Carboxylic Acids

European Journal of Mass Spectrometry ◽

10.1255/ejms.970 ◽

2009 ◽

Vol 15 (2) ◽

pp. 239-248 ◽

Cited By ~ 4

Author(s):

Solveig Gaarn Olesen ◽

Steen Hammerum

Keyword(s):

Hydrogen Bond ◽

Hydrogen Bonds ◽

Bond Strength ◽

Bond Length ◽

Carboxylic Acids ◽

Computational Study ◽

Proton Affinities ◽

Oh Groups ◽

Hydrogen Bond Strength ◽

Length Changes

It is generally expected that the hydrogen bond strength in a D–H•••A adduct is predicted by the difference between the proton affinities (Δ PA) of D and A, measured by the adduct stabilization, and demonstrated by the infrared (IR) redshift of the D–H bond stretching vibrational frequency. These criteria do not always yield consistent predictions, as illustrated by the hydrogen bonds formed by the E and Z OH groups of protonated carboxylic acids. The Δ PA and the stabilization of a series of hydrogen bonded adducts indicate that the E OH group forms the stronger hydrogen bonds, whereas the bond length changes and the redshift favor the Z OH group, matching the results of NBO and AIM calculations. This reflects that the thermochemistry of adduct formation is not a good measure of the hydrogen bond strength in charged adducts, and that the ionic interactions in the E and Z adducts of protonated carboxylic acids are different. The OH bond length and IR redshift afford the better measure of hydrogen bond strength.

Download Full-text