Vibrational Spectra of α-Amino Acids in the Zwitterionic State in Aqueous Solution and the Solid State: DFT Calculations and the Influence of Hydrogen Bonding

A systematic evaluation of the CSD and the PDB in conjunction with DFT calculations reveal that non-covalent Carbon-bonding interactions with X–CH3 can be weakly directional in the solid state (P ≤ 1.5) when X = N or O. This is comparable to very weak CH hydrogen bonding interactions and is in line with the weak interaction energies calculated (≤ –1.5 kcal·mol−1) of typical charge neutral adducts such as [Me3N-CH3···OH2] (2a). The interaction energy is enhanced to ≤–5 kcal·mol−1 when X is more electron withdrawing such as in [O2N-CH3··O=Cdme] (20b) and to ≤18 kcal·mol−1 in cationic species like [Me3O+-CH3···OH2]+ (8a).

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σ-Hole halogen bonding interactions in a mixed valence cobalt(iii/ii) complex and anti-electrostatic hydrogen bonding interaction in a cobalt(iii) complex: a theoretical insight

CrystEngComm ◽

10.1039/c8ce01323c ◽

2018 ◽

Vol 20 (45) ◽

pp. 7281-7292 ◽

Cited By ~ 10

Author(s):

Kousik Ghosh ◽

Klaus Harms ◽

Antonio Bauzá ◽

Antonio Frontera ◽

Shouvik Chattopadhyay

Keyword(s):

Hydrogen Bonding ◽

Solid State ◽

Dft Calculations ◽

Mixed Valence ◽

Halogen Bonding ◽

Supramolecular Interactions ◽

Hydrogen Bonding Interaction ◽

Bonding Interaction ◽

Solid State Structures ◽

Theoretical Insight

Supramolecular interactions in the solid state structures of a mixed valence cobalt(ii/iii) complex and a cobalt(iii) complex have been studied using DFT calculations.

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Hydrogen Bonding Effects on the13C NMR Chemical Shift Tensors of Some Amino Acids in the Solid State

Magnetic Resonance in Chemistry ◽

10.1002/(sici)1097-458x(199709)35:9<606::aid-omr124>3.0.co;2-# ◽

1997 ◽

Vol 35 (9) ◽

pp. 606-608 ◽

Cited By ~ 17

Author(s):

Guang Zheng ◽

Liming Wang ◽

Jianzhi Hu ◽

Xiaodong Zhang ◽

Lianfang Shen ◽

...

Keyword(s):

Amino Acids ◽

Hydrogen Bonding ◽

Solid State ◽

Chemical Shift ◽

Nmr Chemical Shift ◽

Chemical Shift Tensors

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Solid state simulation of tetramer form of 5-aminoorotic acid: The vibrational spectra and molecular structure study by using MP2 and DFT calculations

Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy ◽

10.1016/j.saa.2012.06.048 ◽

2012 ◽

Vol 97 ◽

pp. 948-962 ◽

Cited By ~ 9

Author(s):

S. Ortiz ◽

M. Alcolea Palafox ◽

V.K. Rastogi ◽

Rashmi Tomer

Keyword(s):

Molecular Structure ◽

Solid State ◽

Dft Calculations ◽

Vibrational Spectra ◽

Structure Study

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1,2-O-(Ethane-1,2-diyl)-α-D-glucofuranose. Crystal Structure, and the Stereochemistry of Related Bicyclic Acetal Analogues

Australian Journal of Chemistry ◽

10.1071/ch9960299 ◽

1996 ◽

Vol 49 (3) ◽

pp. 299 ◽

Cited By ~ 1

Author(s):

AM Lebuis ◽

DS Lee ◽

AS Perlin

Keyword(s):

Crystal Structure ◽

Aqueous Solution ◽

Hydrogen Bonding ◽

Solid State ◽

Intermolecular Hydrogen Bonding ◽

Methyl Substituent ◽

Spectroscopic Evidence

Crystalline 1,2-O-(ethane-1,2-diyl)-α-D- glucofuranose (9) is orthorhombic, P 21212, with a = 17.702(4), b = 8.892(2), c = 5.6400(9) Ǻ, Z = 4, R = 0.050, and Rw = 0.041. The conformation of the 1,4-dioxan ring in this bicyclic acetal is slightly distorted from 7C1, and that of the glucofuranose ring is intermediate between the 3E and 3T2 conformations. Extensive intermolecular hydrogen-bonding of exocyclic OH(5) and OH(6) dominates the solid state interactions. In aqueous solution, compound (9) retains close to the same stereochemical characteristics as in the crystal, including those of the exocyclic C(4)-C(5)-C(6) segment of the molecule, according to n.m.r. spectroscopic evidence. These findings provide support for the structures assigned to related bicyclic acetals (7) and (8), which differ from (9) in having a methyl substituent at C(8) on their 1,4-dioxan rings, notably in confirming that the configuration at C(8) is R in (7) and S in (8).

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