THE BASICITIES OF ORTHO-SUBSTITUTED BENZOIC ACIDS

1961 ◽  
Vol 39 (12) ◽  
pp. 2508-2515 ◽  
Author(s):  
Ross Stewart ◽  
Maurice R. Granger
Keyword(s):  
Hydrogen Bonding ◽  
Benzoic Acid ◽  
Sulphuric Acid ◽  
Benzoic Acids ◽  
Methyl Ethyl ◽  
Alkyl Groups ◽  
Substituted Benzoic Acids

The basicities of 15 ortho-substituted benzoic acids have been measured in sulphuric acid. The ortho effects of alkyl groups are base weakening and increase in the expected order methyl, ethyl, i-propyl, t-butyl. Ortho halo benzoic acids have comparable basicities and are weaker than their para isomers. Oxygen-containing ortho substituents, except hydroxyl, all cause substantial base strengthening relative to the para isomers. Even the groups nitro and carboxyl when substituted ortho in benzoic acid cause the basicity to rise, presumably because of hydrogen bonding in the conjugate acids.

Mixed-dimer formation in binary systems of 4-substituted benzoic acids and structure considerations

2008 ◽  
Vol 86 (6) ◽  
pp. 525-532 ◽  
Author(s):  
Maren Roman ◽  
Annett Kaeding-Koppers ◽  
Peter Zugenmaier
Keyword(s):  
Benzoic Acid ◽  
Crystalline Phase ◽  
Liquid Crystalline ◽  
Binary Systems ◽  
Benzoic Acids ◽  
Dimer Formation ◽  
Crystalline Phases ◽  
Cholesteric Phase ◽  
Liquid Crystalline Phases ◽  
Substituted Benzoic Acids

The phase behavior of binary systems of 4-substituted benzoic acids is governed by the formation of mixed dimers. This study was conducted to determine the effect of the components’ structural difference on mixed-dimer formation in crystalline and liquid-crystalline phases. The phase diagrams of two systems, with 4-[(S)-(–)-2-methylbutoxy]benzoic acid (MBOBA) as one component and 4-(hex-5-enoxy)benzoic acid (HOBA) and 4-(dec-9-enoxy)benzoic acid (DOBA), respectively, as the second component, were determined by differential scanning calorimetry, polarized-light microscopy, and X-ray diffraction. The MBOBA-HOBA system exhibited a cholesteric phase, two solid solutions, and above 58 °C for compositions between 40 and 80 mol% HOBA a crystalline phase of mixed dimers. The MBOBA-DOBA system showed a crystalline phase of mixed dimers at all compositions, a cholesteric phase, and a twisted smectic C phase, which was dominated by mixed dimers at 60 and 70 mol% DOBA. We conclude that liquid-crystalline phases are generally dominated by mixed dimers, but in crystalline phases the formation of mixed dimers is promoted by a greater difference in molecular structure. The crystal structure of two of the pure compounds MBOBA and DOBA and comparable compounds have been determined for an evaluation of the arrangements of the molecules in the crystal and liquid-crystalline state.Key words: benzoic acid, crystal arrangement, phase diagrams, liquid crystal.

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.

Electrochemical Reduction of Benzoic Acid and Substituted Benzoic Acids in Some Room Temperature Ionic Liquids

2008 ◽  
Vol 112 (33) ◽  
pp. 12966-12973 ◽  
Author(s):  
Debbie S. Silvester ◽  
Weisi He ◽  
Leigh Aldous ◽  
Christopher Hardacre ◽  
Richard G. Compton
Keyword(s):  
Ionic Liquids ◽  
Benzoic Acid ◽  
Electrochemical Reduction ◽  
Room Temperature ◽  
Room Temperature Ionic Liquids ◽  
Benzoic Acids ◽  
Substituted Benzoic Acids

scholarly journals Thermodynamics of Ionization of Benzoic Acid and Some Substituted Benzoic Acids in 1,4-Dioxane--Water Mixtures.

1992 ◽  
Vol 46 ◽  
pp. 399-402 ◽  
Author(s):  
Dattatraya Vyankatesh Jahagirdar ◽  
Harri Lönnberg ◽  
S. Grundvig ◽  
Yngve Stenstrøm ◽  
Agha Zul-Quarnain Khan ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Benzoic Acids ◽  
Substituted Benzoic Acids ◽  
Thermodynamics Of Ionization
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