THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY ULTRAVIOLET LIGHT ABSORPTION: PART II. THE EFFECT OF SOLVENT–SOLUTE INTERACTIONS ON THE INTERMOLECULAR: HYDROGEN BOND IN BENZOIC ACIDS

1959 ◽  
Vol 37 (2) ◽  
pp. 334-340 ◽  
Author(s):  
W. F. Forbes ◽  
A. R. Knight
Keyword(s):  
Hydrogen Bonding ◽  
Intermolecular Hydrogen Bond ◽  
Solvent Mixtures ◽  
Benzoic Acids ◽  
Intermolecular Hydrogen Bonding ◽  
Absorption Bands ◽  
Effect Of Solvent ◽  
Concentration Dependences ◽  
Solute Interactions ◽  
Substituted Benzoic Acids

The concentration dependence of some electronic absorption bands, which has previously been ascribed to intermolecular hydrogen bonding, is reinvestigated. The concentration dependences are compared for a number of substituted benzoic acids in inert solvents, and in solvent mixtures containing various amounts of ether. The results are discussed in terms of current theories of hydrogen bonding.

Molecular Cocrystals of Carboxylic Acids. XXVI Adducts of the Amino-Substituted Benzoic Acids with Nitroaromatic Lewis Bases: the Influence of Associative Polyfunctional Substituents on Self-Assembly of Molecules in Cocrystallization Processes

1997 ◽  
Vol 50 (10) ◽  
pp. 977 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Self Assembly ◽  
Benzoic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Lewis Bases ◽  
Aminobenzoic Acids ◽  
Substituted Benzoic Acids

A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroquinoline and 5-nitroisoquinoline has been prepared and characterized by using infrared spectroscopy and X-ray powder diffraction, and in four cases by single-crystal X-ray diffraction methods. These four compounds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)(C9H6N2O2)], 4-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)2(C9H6N2O2)], 2-aminobenzoic acid with 5-nitroisoquinoline [(C7H7NO2)(C9H6N2O2)] and 4-aminobenzoic acid with 5-nitroisoquinoline [(C7H7N2O2)(C9H6N2O2)]. Other compounds described are the (1 : 1) adducts of 4-aminobenzoic acid with 2-chloro-5-nitropyridine, and 2-aminobenzoic acid with 5-nitroquinoline. All adducts involve hydrogen-bonding network associations while in none of the examples is any proton transfer involved.

A comparative study on the dynamics of epimeric 1-hydroxymethyl quinolizidines: II. The solvent and concentration dependence of the association properties

1988 ◽  
Vol 66 (9) ◽  
pp. 2166-2171 ◽  
Author(s):  
K. Kulińska ◽  
M. Wiewiórowski
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Intermolecular Hydrogen Bond ◽  
Chloroform Solution ◽  
Weak Acid ◽  
Hydroxyl Group ◽  
Intermolecular Hydrogen Bonding ◽  
Concentrated Solutions ◽  
Electron Pairs ◽  
Solvent Molecules

The homo and heteroassociation patterns of lupinine and epilupinine in different solvents and at various concentrations have been studied. In n-hexane, n-heptane, CCl4, and C2H4Cl2 solvents, lupinine monomers with an intramolecular OH … N hydrogen bond dominate over homoassociates with an OH … O′ intermolecular hydrogen bond even in concentrated solutions. Homoassociation of lupinine by intermolecular OH … N′ hydrogen bonding is observed only in saturated solutions. In chloroform solution any intermolecular homoassociation is effectively blocked because of significant affinity of chloroform molecules acting as a weak acid toward the free electron pairs of the oxygen atom from the hydroxyl group that would be otherwise engaged in intramolecular OH … N hydrogen bonding. Epilupinine in n-hexane, n-heptane, CCl4, C2H4Cl2, and chloroform solutions forms possible homoassociates both by OH … N′ and OH … O′ intermolecular hydrogen bonding. In dioxane-d8, DMSO, and D2O solvents both lupinine and epilupinine form heteroassociates with solvent molecules.

scholarly journals Structure Elucidation of N-aryl-2-chloro-3-oxobutanamides with respect to intra- and intermolecular hydrogen bonding

2002 ◽  
Vol 2002 (1) ◽  
pp. 13-14 ◽  
Author(s):  
Petra Frohberg ◽  
Guntram Drutkowski ◽  
Christoph Wagner ◽  
Olaf Lichtenberger
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Solid State ◽  
Structure Elucidation ◽  
Intermolecular Hydrogen Bond ◽  
Carbonyl Oxygen ◽  
Intermolecular Hydrogen Bonding ◽  
Intramolecular Association

In general, N-aryl-2-chloro-3-oxobutanamides form in solid state an intermolecular hydrogen bond between the anilide hydrogen and the anilide carbonyl oxygen of a neighbouring molecule, which is disrupted in solution. An intramolecular association could not be detected.

scholarly journals Molecular Structure, Spectral Investigations, Hydrogen Bonding Interactions and Reactivity-Property Relationship of Caffeine-Citric Acid Cocrystal by Experimental and DFT Approach

2021 ◽  
Vol 9 ◽  
Author(s):  
Priya Verma ◽  
Anubha Srivastava ◽  
Karnica Srivastava ◽  
Poonam Tandon ◽  
Manishkumar R. Shimpi
Keyword(s):  
Hydrogen Bonding ◽  
Citric Acid ◽  
Electrostatic Potential ◽  
Energy Gap ◽  
Intermolecular Hydrogen Bond ◽  
Active Form ◽  
Intermolecular Hydrogen Bonding ◽  
Scanning Calorimetry ◽  
Property Relationship ◽  
Hydrogen Bonding Interactions

The pharmaceutical cocrystal of caffeine-citric acid (CAF-CA, Form II) has been studied to explore the presence of hydrogen bonding interactions and structure-reactivity-property relationship between the two constituents CAF and Citric acid. The cocrystal was prepared by slurry crystallization. Powder X-ray diffraction (PXRD) analysis was done to characterize CAF-CA cocrystal. Also, differential scanning calorimetry (DSC) confirmed the existence of CAF-CA cocrystal. The vibrational spectroscopic (FT-IR and FT-Raman) signatures and quantum chemical approach have been used as a strategy to get insights into structural and spectral features of CAF-CA cocrystal. There was a good correlation among the experimental and theoretical results of dimer of cocrystal, as this model is capable of covering all nearest possible interactions present in the crystal structure of cocrystal. The spectroscopic results confirmed that (O33-H34) mode forms an intramolecular (C25 = O28∙∙∙H34-O33), while (O26-H27) (O39-H40) and (O43-H44) groups form intermolecular hydrogen bonding (O26-H27∙∙∙N24-C22, O39-H40∙∙∙O52 = C51 and O43-H44∙∙∙O86 = C83) in cocrystal due to red shifting and increment in bond length. The quantum theory of atoms in molecules (QTAIM) analysis revealed (O88-H89∙∙∙O41) as strongest intermolecular hydrogen bonding interaction with interaction energy −12.4247 kcal mol−1 in CAF-CA cocrystal. The natural bond orbital analysis of the second-order theory of the Fock matrix highlighted the presence of strong interactions (N∙∙∙H and O∙∙∙H) in cocrystal. The HOMO-LUMO energy gap value shows that the CAF-CA cocrystal is more reactive, less stable and softer than CAF active pharmaceutical ingredients. The electrophilic and nucleophilic reactivities of atomic sites involved in intermolecular hydrogen bond interactions in cocrystal have been demonstrated by mapping electron density isosurfaces over electrostatic potential i.e. plotting molecular electrostatic potential (MESP) map. The molar refractivity value of cocrystal lies within the set range by Lipinski and hence it may be used as orally active form. The results show that the physicochemical properties of CAF-CA cocrystal are enhanced in comparison to CAF (API).

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