Solvency and hydrogen bonding interactions in nonaqueous systems.

Abstract A study of the importance of hydrogen-bonding interactions in the formation of complexes is useful in providing knowledge of the physical and chemical properties of drug molecules and hopefully it will eventually lead to rational formulation of drugs into suitable dosage forms. The present report deals with a study of some of the methods available for the experimental measurement of these interactions and the means of determining the association (equilibrium) constants from the experimental results. An attempt is made to develop suitable methods for the quantitative analysis of hydrogen-bonding data so that useful estimates of association constants can be made a priori. The effect of the non-aqueous solvent on the value of the association constant is also discussed and a method is given whereby an estimate of solvent interaction can be calculated.

[1]  M. Tsuboi,et al.  Spectroscopic investigation of the strength of hydrogen bonds formed by amides , 1955 .

[2]  S. Ghersetti,et al.  Infrared study of hydrogen bonding between various phenols and diphenyl—sulphoxide: Thermodynamic properties , 1965 .

[3]  R. S. Mulliken.  Molecular Compounds and their Spectra. II , 1952 .

[4]  H. H. Jaffé,et al.  A Reëxamination of the Hammett Equation. , 1953 .

[5]  R. Drago,et al.  The Validity of Frequency Shift-Enthalpy Correlations. I. Adducts of Phenol with Nitrogen and Oxygen Donors , 1962 .

[6]  R. S. Mulliken.  MOLECULAR COMPOUNDS AND THEIR SPECTRA. 3. THE INTERACTION OF ELECTRON DONORS AND ACCEPTORS , 1952 .

[7]  G. Pimentel.  The Bonding of Trihalide and Bifluoride Ions by the Molecular Orbital Method , 1951 .

[8]  A. K. Chandra,et al.  EQUILIBRIUM CONSTANT OF A HYDROGEN BONDING SYSTEM: PHENOL-PYRIDINE , 1962 .

[9]  V. Mutt,et al.  Studies of Hydrogen Bonding. Part II. Intermolecular Hydrogen Bond Association between Organophosphorus Compounds and Methanol, a-Naphthol and Pentachlorophenol, respectively. , 1961 .

[10]  H. W. Thompson,et al.  Intermolecular forces and solvent effects I. Frequency shifts , 1960, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[11]  N. Mataga,et al.  Charge transfer and proton transfer reactions in the excited hydrogen bonded complex in non-polar solvents , 1964 .

[12]  M. Davies,et al.  The determination of molecular association equilibria from distribution and related measurements , 1956 .

[13]  L. J. Bellamy,et al.  Solvent effects on infra-red group frequencies , 1960, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[14]  F. Takahashi,et al.  Solvent effects in ultraviolet spectral studies of hydrogen bonding between phenol and N,N-dimethylacetamide , 1967 .

[15]  C. Rao,et al.  Spectroscopic studies of hydrogen bonding in donor-acceptor systems , 1966 .

[16]  L. E. Sutton,et al.  An investigation of complex formation by partition of a reactant between the vapour phase and solution : the determination of association constants and the heats of formation of some hydrogen bonds , 1955 .

[17]  G. Schwarzenbach.  The Determination of Stability Constants , 1962 .

[18]  T. Higuchi,et al.  Calculation of stability constants of hydrogen-bonded complexes from proton magnetic resonance data. Interactions of phenol with dimethylacetamide and various ketones. Solvent effect , 1967 .

[19]  T. Gramstad,et al.  Studies of hydrogen bonding—XV. The influence of a SP bond in phosphoryl compounds on the PO stretching frequency and their hydrogen bonding ability , 1965 .

[20]  D. L. Powell,et al.  Hydrogen Bonding Studies. IX. The Thermodynamics of Hydrogen Bonding of Phenol to Ethers and Related Compounds , 1964 .

[21]  L. Hammett,et al.  Physical organic chemistry , 1940 .

[22]  M. Gouterman,et al.  Effect of Hydrogen Bonding on the Near Ultraviolet Absorption of Naphthol , 1957 .

[23]  L. Pauling.  The Nature Of The Chemical Bond , 1939 .

[24]  T. Gramstad,et al.  Studies of hydrogen bonding—XVI the complexing of pentafluorophenol with triphenylphosphine oxide , 1966 .

[25]  L. Craig,et al.  Distribution studies; attainment of equilibrium. , 1948, Journal of Biological Chemistry.

[26]  Carl Djerassi,et al.  Optical rotatory dispersion , 1961 .

[27]  W. Schneider,et al.  ON THE PROTON MAGNETIC RESONANCE SHIFT DUE TO HYDROGEN BONDING , 1957 .

[28]  R. J. Bishop,et al.  1172. The study of the equilibrium constant of complex formation between phenol and pyridine in solution by a dielectric constant method , 1964 .

[29]  R. Mecke.  Infra-red spectra of hydroxylic compounds , 1950 .

[30]  T. Higuchi,et al.  Determination of stability constants from optical rotatory dispersion measurements. Camphor-phenol system in carbon tetrachloride. , 1965, Journal of pharmaceutical sciences.

[31]  I. Kuntz,et al.  Molecular interactions and the Benesi-Hildebrand equation , 1968 .

[32]  N. Coggeshall.  Electrostatic Interaction in Hydrogen Bonding , 1950 .

[33]  T. Gramstad.  Studies ot hydrogen bonding—part IX: The effect of solvent interaction on hydrogen bonding , 1963 .

[34]  Satoshi Suzuki,et al.  Electronic Spectra and Hydrogen Bonding. I. Phenol and Naphthols , 1961 .

[35]  R. West,et al.  Hydrogen-bonding studies—VII: Near infrared spectroscopic studies of the intermolecular hydrogen bonding of phenol, p-cresol and p-chlorophenol , 1961 .

[36]  P. Schleyer,et al.  Solvent Effects in Infrared Spectroscopic Studies of Hydrogen Bonding , 1963 .

[37]  G. Eglinton,et al.  939. The association of ortho-substituted phenols with ethers , 1961 .

[38]  L. Larsson,et al.  Intermolecular Hydrogen Bond Association between Phenol and Organophosphorus Compounds. , 1960 .

[39]  B. Wojtkowiak,et al.  N° 83 — Détermination des énergies de liaisons hydrogène formées entre le phénol et diverses bases dans le tétrachlorure de carbone solvant , 1968 .

[40]  J. Pople,et al.  Molecular association in liquids II. A theory of the structure of water , 1951, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[41]  Roger Hayward,et al.  The Hydrogen Bond , 1960 .

[42]  S. Nagakura.  Molecular Complexes and their Spectra. VIII. The Molecular Complex between Iodine and Triethylamine1 , 1958 .

[43]  W. M. Latimer,et al.  POLARITY AND IONIZATION FROM THE STANDPOINT OF THE LEWIS THEORY OF VALENCE. , 1920 .

[44]  J. Plíva,et al.  Studies of solute-solvent interactions—I. General considerations , 1965 .

[45]  H. Flood,et al.  Studies of Hydrogen Bonding. Part III. Intermolecular Hydrogen Bond Association between Nitrogen Compounds and Methanol, Phenol, alpha-Naphthol and Pentachlorophenol. , 1962 .

[46]  H. Taylor.  A treatise on physical chemistry , 1924 .

[47]  H. Flood,et al.  Studies of Hydrogen Bonding. Part V. The Intermolecular Hydrogen Bond Association of Amides with Phenol and Pentachlorophenol. , 1962 .

[48]  K. Purcell,et al.  Theoretical aspects of the linear enthalpy wavenumber shift relation for hydrogen-bonded phenols , 1967 .

[49]  Mitsuo. Ito.  Ultraviolet absorption study of the molecular association of phenols , 1960 .

[50]  J. Widom,et al.  A Study of the Association of Phenol with Several Ketones by Infrared Absorption Measurements , 1957 .

[51]  P. R. Wells,et al.  Linear Free Energy Relationships , 1968 .

[52]  D. L. Powell,et al.  Hydrogen bonding studies—VIII. The thermodynamics of hydrogen bonding of phenol to some oxygen-containing molecules and to benzene☆ , 1964 .

[53]  H. Baba.  Hydrogen Bonding Effect on the Electronic Absorption Spectrum of p-Hydroxyazobenzene , 1958 .

[54]  N. Coggeshall,et al.  Infrared Absorption Study of Hydrogen Bonding Equilibria , 1951 .

[55]  W. Schneider,et al.  NUCLEAR MAGNETIC RESONANCE MEASUREMENTS OF COMPLEXES OF CHLOROFORM WITH AROMATIC MOLECULES AND OLEFINS , 1957 .

[56]  Norman C. Li,et al.  Chloroform as hydrogen donor to some organophosphorus compounds and long-chain tertiary alkylamines , 1968 .

[57]  E. Ōsawa,et al.  Hydrogen Bonding of Phenol to π Electrons of Aromatics, Polyolefins, Heteroaromatics, Fulvenes, and Azulenes1 , 1966 .

[58]  E. Becker.  Infrared studies of the self-association of chloroform , 1959 .

[59]  T. Gramstad.  Studies of hydrogen bonding—part VII: Hydrogen-bond association of phenol and pentachlorophenol with carbonyl compounds and ethers , 1963 .

[60]  S. Bratŏz.  Electronic Theories of Hydrogen Bonding , 1967 .