Competing Intramolecular Vs. Intermolecular Hydrogen Bonds in Solution

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2014 Oct 30

PMID 25353178

Citations 27

Authors

Peter I Nagy

Affiliations

Soon will be listed here.

Abstract

A hydrogen bond for a local-minimum-energy structure can be identified according to the definition of the International Union of Pure and Applied Chemistry (IUPAC recommendation 2011) or by finding a special bond critical point on the density map of the structure in the framework of the atoms-in-molecules theory. Nonetheless, a given structural conformation may be simply favored by electrostatic interactions. The present review surveys the in-solution competition of the conformations with intramolecular vs. intermolecular hydrogen bonds for different types of small organic molecules. In their most stable gas-phase structure, an intramolecular hydrogen bond is possible. In a protic solution, the intramolecular hydrogen bond may disrupt in favor of two solute-solvent intermolecular hydrogen bonds. The balance of the increased internal energy and the stabilizing effect of the solute-solvent interactions regulates the new conformer composition in the liquid phase. The review additionally considers the solvent effects on the stability of simple dimeric systems as revealed from molecular dynamics simulations or on the basis of the calculated potential of mean force curves. Finally, studies of the solvent effects on the type of the intermolecular hydrogen bond (neutral or ionic) in acid-base complexes have been surveyed.

Citing Articles

Mg-Ion Dependence Revealed for a BAHD 13--β-Aminoacyltransferase from Plants.

Al-Hilfi A, Li Z, Merz Jr K, Walker K JACS Au. 2024; 4(11):4249-4262.

PMID: 39610752 PMC: 11600153. DOI: 10.1021/jacsau.4c00577.

Theoretical Analysis of Coordination Geometries in Transition Metal-Histidine Complexes Using Quantum Chemical Calculations.

Zhang D, Kishimoto N Molecules. 2024; 29(13).

PMID: 38998956 PMC: 11243457. DOI: 10.3390/molecules29133003.

Elucidating the Non-Covalent Interactions that Trigger Interdigitation in Lead-Halide Layered Hybrid Perovskites.

Maufort A, Cerda J, Van Hecke K, Deduytsche D, Verding A, Ruttens B Inorg Chem. 2024; 63(12):5568-5579.

PMID: 38470041 PMC: 10967955. DOI: 10.1021/acs.inorgchem.3c04536.

Development of Taste Sensor with Lipid/Polymer Membranes for Detection of Umami Substances Using Surface Modification.

Yuan W, Zhao Z, Kimura S, Toko K Biosensors (Basel). 2024; 14(2).

PMID: 38392014 PMC: 10887241. DOI: 10.3390/bios14020095.

Self-assembled Janus base nanotubes: chemistry and applications.

Zhang W, Chen Y Front Chem. 2024; 11:1346014.

PMID: 38374885 PMC: 10876059. DOI: 10.3389/fchem.2023.1346014.

References

Ishiuchi S, Asakawa T, Mitsuda H, Miyazaki M, Chakraborty S, Fujii M . Gas-phase spectroscopy of synephrine by laser desorption supersonic jet technique. J Phys Chem A. 2011; 115(37):10363-9. DOI: 10.1021/jp205267c. View

Yamabe S, Tsuchida N . A computational study of interactions between acetic acid and water molecules. J Comput Chem. 2003; 24(8):939-47. DOI: 10.1002/jcc.10178. View

Patel S, Brooks 3rd C . CHARMM fluctuating charge force field for proteins: I parameterization and application to bulk organic liquid simulations. J Comput Chem. 2003; 25(1):1-15. DOI: 10.1002/jcc.10355. View

Forti F, Cavasotto C, Orozco M, Barril X, Luque F . A Multilevel Strategy for the Exploration of the Conformational Flexibility of Small Molecules. J Chem Theory Comput. 2015; 8(5):1808-19. DOI: 10.1021/ct300097s. View

Mollendal H, Samdal S, Guillemin J . Microwave spectrum and intramolecular hydrogen bonding of 2-isocyanoethanol (HOCH(2)CH(2)N≡C). J Phys Chem A. 2014; 118(17):3120-7. DOI: 10.1021/jp502212n. View

Contreras-Garcia J, Yang W, Johnson E . Analysis of hydrogen-bond interaction potentials from the electron density: integration of noncovalent interaction regions. J Phys Chem A. 2011; 115(45):12983-90. PMC: 3651877. DOI: 10.1021/jp204278k. View

Alagona G, Ghio C, Nagy P . Theoretical Conformational Analysis for Neurotransmitters in the Gas Phase and in Aqueous Solution. Serotonin. J Chem Theory Comput. 2015; 1(5):801-16. DOI: 10.1021/ct050088c. View

Molinaro A, de Castro C, Lanzetta R, Manzo E, Parrilli M . Solvent effect on the isomeric equilibrium of carbohydrates: the superior ability of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization. J Am Chem Soc. 2001; 123(50):12605-10. DOI: 10.1021/ja016471i. View

Nagy P . Theoretical studies of the solvent effect on the conformation of the HO-C-C-X (X = F, NH2, NO2) moiety with competing intra- and intermolecular hydrogen bonds. J Phys Chem A. 2012; 116(29):7726-41. DOI: 10.1021/jp304164g. View

10.

Long J, Harris N, Lammertsma K . Formaldehyde oxime <--> nitrosomethane tautomerism. J Org Chem. 2001; 66(20):6762-7. DOI: 10.1021/jo010671v. View

11.

Alagona G, Ghio C, Nagy P . The catalytic effect of water on the keto-enol tautomerism. Pyruvate and acetylacetone: a computational challenge. Phys Chem Chem Phys. 2010; 12(35):10173-88. DOI: 10.1039/c003999c. View

12.

Klein R . Ab initio conformational studies on diols and binary diol-water systems using DFT methods. Intramolecular hydrogen bonding and 1:1 complex formation with water. J Comput Chem. 2002; 23(6):585-99. DOI: 10.1002/jcc.10053. View

13.

Alonso J, Perez C, Eugenia Sanz M, Lopez J, Blanco S . Seven conformers of L-threonine in the gas phase: a LA-MB-FTMW study. Phys Chem Chem Phys. 2009; 11(4):617-27. DOI: 10.1039/b810940k. View

14.

Nagy P, Alagona G, Ghio C, Takacs-Novak K . Theoretical conformational analysis for neurotransmitters in the gas phase and in aqueous solution. Norepinephrine. J Am Chem Soc. 2003; 125(9):2770-85. DOI: 10.1021/ja028952n. View

15.

Nagy P, Erhardt P . On the interaction of aliphatic amines and ammonium ions with carboxylic acids in solution and in receptor pockets. J Phys Chem B. 2012; 116(18):5425-36. DOI: 10.1021/jp300588q. View

16.

Nagy P . Theoretical study of the gauche-trans equilibrium with and without an intramolecular hydrogen bond for +H3NCH2CH2X systems (X = OH, NH2, COO-) in solution. Phys Chem Chem Phys. 2012; 14(40):13955-62. DOI: 10.1039/c2cp42240a. View

17.

Petterson K, Stein R, Drake M, Roberts J . An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution. Magn Reson Chem. 2005; 43(3):225-30. DOI: 10.1002/mrc.1512. View

18.

Haufa K, Antoni Czarnecki M . Molecular structure and hydrogen bonding of 2-aminoethanol, 1-amino-2-propanol, 3-amino-1-propanol, and binary mixtures with water studied by Fourier transform near-infrared spectroscopy and density functional theory calculations. Appl Spectrosc. 2010; 64(3):351-8. DOI: 10.1366/000370210790918445. View

19.

Lutgens M, Friedriszik F, Lochbrunner S . Direct observation of the cyclic dimer in liquid acetic acid by probing the C=O vibration with ultrafast coherent Raman spectroscopy. Phys Chem Chem Phys. 2014; 16(33):18010-6. DOI: 10.1039/c4cp01740d. View

20.

Orozco M, Luque F . Theoretical Methods for the Description of the Solvent Effect in Biomolecular Systems. Chem Rev. 2001; 100(11):4187-4226. DOI: 10.1021/cr990052a. View