Nearest-neighbor and non-nearest-neighbor interactions between substituents in the benzene ring. Experimental and theoretical study of functionally substituted benzamides

Journal of Physical Chemistry A

Volumn 120, Issue 49, 2016, Pages 9867-9877

  Verevkin, Sergey P ^a   Emel'yanenko, Vladimir N ^a,b   Nagrimanov, Ruslan N ^b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b KAZAN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; BENZENE; HYDROSTATIC PRESSURE; QUANTUM CHEMISTRY; TEMPERATURE DISTRIBUTION; VAPORIZATION;

COMBUSTION CALORIMETRY; ENTHALPIES OF FORMATION; NEAREST-NEIGHBOR INTERACTIONS; QUANTUM-CHEMICAL METHODS; STANDARD MOLAR ENTHALPIES OF FORMATIONS; STANDARD MOLAR ENTHALPY; TEMPERATURE DEPENDENCE; TRANSPIRATION METHODS;

ENTHALPY;

EID: 85017163995     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/acs.jpca.6b10332     Document Type: Article

References (58)

1. Krygowski, T. M.; Stepien, B. T. Sigma- and Pi-Electron Delocalization: Focus on Substituent Effects. Chem. Rev. 2005, 105, 3482-3512.
2. Sunoj, R. B. Theoretical Aspects of Organoselenium Chemistry. In Patai's Chemistry of Functional Groups: Organic Selenium and Tellurium Compounds, Vol. 3; John Wiley & Sons: UK, 2011.
3. Verevkin, S. P. Thermochemistry of Phenols. Quantification of the Ortho-, Para-, and Meta-interactions in Tert-alkyl Substituted Phenols. J. Chem. Thermodyn. 1999, 31, 559-585.
4. Verevkin, S. P.; Emel'yanenko, V. N.; Klamt, A. Thermochemistry of Chlorobenzenes and Chlorophenols: Ambient Temperature Vapor Pressures and Enthalpies Phase Transitions. Experiment and Calculations. J. Chem. Eng. Data 2007, 52, 499-510.
5. Verevkin, S. P.; Melkhanova, S. V.; Emel'yanenko, V. N.; Zaitsau, D. H.; Varfolomeev, M. A.; Solomonov, B. N.; Zherikova, K. V. Thermochemistry of dihalogen-substituted benzenes: data evaluation using experimental and quantum chemical methods. J. Phys. Chem. B 2014, 118, 14479-14492.
6. Verevkin, S. P.; Emel'yanenko, V. N.; Diky, V.; Muzny, C. D.; Chirico, R. D.; Frenkel, M. New Group Contribution Approach to Thermochemical Properties of Organic Compounds: Hydrocarbons and Oxygen Containing Compounds. J. Phys. Chem. Ref. Data 2013, 42, 033102.
7. Verevkin, S. P. Improved Group-Additivity Values for the Estimation of the Standard Enthalpies of Formation of Imines and Carboxylic Acids Derivatives. J. Therm. Anal. Calorim. 2000, 60, 437-451.
8. Zherikova, K. V.; Svetlov, A. A.; Emel'yanenko, V. N.; Held, C.; Verevkin, S. P. Thermochemistry of halogenobenzoic acids as an access to PC-SAFT solubility modeling. Fluid Phase Equilib. 2016, 409, 399-407.
9. Verevkin, S. P.; Zaitsau, D. H.; Emel'yanenko, V. N.; Stepurko, E. N.; Zherikova, K. V. Benzoic acid derivatives: evaluation of thermochemical properties with complementary experimental and computational methods. Thermochim. Acta 2015, 622, 18-30.
10. Ryskalieva, A. K.; Abramova, G. V.; Erkasov, R.; Sh; Nurakhmetov, N. N. Enthalpies of combustion and formation of salicylic acid derivatives. Russ. J. Phys. Chem. (Engl. Transl.) 1992, 66, 421-423.
11. Ribeiro da Silva, M. D. M. C.; Araújo, N. R. M. Thermochemical studies on salicylaldehyde and salicylamide. J. Chem. Thermodyn. 2007, 39, 1372-1376.
12. Nordström, F. L.; Rasmuson, A. C. Solubility and Melting Properties of Salicylamide. J. Chem. Eng. Data 2006, 51, 1775-1777.
13. 3) Compounds. J. Phys. Chem. A 2008, 112, 10029-10039.
14. Almeida, A. R. R. P.; Monte, M. J. S. Thermodynamic Study of Benzamide, N-Methylbenzamide, and N,N-Dimethylbenzamide: Vapor Pressures, Phase Diagrams, and Hydrogen Bond Enthalpy. J. Chem. Eng. Data 2010, 55, 3507-3512.
15. Almeida, A. R. R. P.; Monte, M. J. S. Thermodynamic Study of the Three Fluorobenzamides: Vapor Pressures, Phase Diagrams, and Hydrogen Bonds. J. Chem. Eng. Data 2010, 55, 5230-5236.
16. Almeida, A. R. R. P.; Matos, M. A. R.; Monte, M. J. S.; Morais, V. M. F. Experimental and computational thermodynamic study of ortho-, meta-, and para-methylbenzamide. J. Chem. Thermodyn. 2012, 47, 81-89.
17. Almeida, A. R. R. P.; Monte, M. J. S.; Matos, M. A. R.; Morais, V. M. F. Experimental and computational thermodynamic study of ortho- meta- and para-aminobenzamide. J. Chem. Thermodyn. 2013, 59, 222-232.
18. Almeida, A. R. R. P.; Monte, M. J. S.; Matos, M. A. R.; Morais, V. M. F. The thermodynamic stability of the three isomers of methoxybenzamide: An experimental and computational study. J. Chem. Thermodyn. 2014, 73, 12-22.
19. Verevkin, S. P.; Emel'yanenko, V. N. Transpiration method: Vapor pressures and enthalpies of vaporization of some low-boiling esters. Fluid Phase Equilib. 2008, 266, 64-75.
20. Verevkin, S. P.; Sazonova, A. Y.; Emel'yanenko, V. N.; Zaitsau, D. H.; Varfolomeev, M. A.; Solomonov, B. N.; Zherikova, K. V. Thermochemistry of halogen-substituted methylbenzenes. J. Chem. Eng. Data 2015, 60, 89-103.
21. Emel'yanenko, V. N.; Verevkin, S. P. Benchmark thermodynamic properties of 1,3-Propanediol: comprehensive experimental and theoretical study. J. Chem. Thermodyn. 2015, 85, 111-119.
22. Verevkin, S. P.; Schick, C. Substituent effects on the benzene ring. Determination of the intra-molecular interactions of substituents in tert-alkyl substituted catechols from thermochemical measurements. J. Chem. Eng. Data 2000, 45, 946-952.
23. Emel'yanenko, V. N.; Verevkin, S. P.; Heintz, A. The gaseous enthalpy of formation of the ionic liquid 1-butyl-3-methylimidazolium dicyanamide from combustion calorimetry, vapor pressure measurements, and ab initio calculations. J. Am. Chem. Soc. 2007, 129, 3930-3937.
24. Hubbard, W. N.; Scott, D. W.; Waddington, G. Standard States Corrections for Combustions in a Bomb at Constant Volume. In Experimental Thermochemistry; Rossini, F. D., Ed.; Interscience: New York, 1956; pp 75-127.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al.. Gaussian 09, Revision A.02; Gaussian Inc.: Wallingford, CT, 2009.
26. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Gaussian-4 Theory. J. Chem. Phys. 2007, 126, 084108.
27. Verevkin, S. P.; Emel'yanenko, V. N.; Notario, R.; Roux, M. V.; Chickos, J. S.; Liebman, J. F. Rediscovering the wheel. Thermochemical analysis of energetics of the aromatic diazines. J. Phys. Chem. Lett. 2012, 3, 3454-3459.
28. Rayne, S.; Forest, K. Estimated Gas-Phase Standard State Enthalpies of Formation for Organic Compounds Using the Gaussian-4 (G4) and W1bd Theoretical Methods. J. Chem. Eng. Data 2010, 55, 5359-5364.
29. Chickos, J. S.; Acree, W. E. Enthalpies of Sublimation of Organic and Organometallic Compounds. 1910-2001. J. Phys. Chem. Ref. Data 1999, 31, 537-698.
30. Chickos, J. S.; Hosseini, S.; Hesse, D. G.; Liebman, J. F. Heat capacity corrections to a standard state: a comparison of new and some literature methods for organic liquids and solids. Struct. Chem. 1993, 4, 271-278.
31. Aihara, A. Estimation of the Energy of Hydrogen Bonds Formed in Crystals. III. Amides. Bull. Chem. Soc. Jpn. 1960, 33, 1188-1194.
32. Gomez, L. A. T.; Sabbah, R. Thermodynamique de substances azotees. IX. Etude thermochimique de la benzamide. Comparaison des grandeurs energetiques liees a la structure de quelques amides et thioamides. Thermochim. Acta 1982, 58, 311-315.
33. Manin, A. N.; Voronin, A. P.; Perlovich, G. L. Thermodynamic and structural aspects of hydroxybenzamide molecular crystals study. Thermochim. Acta 2013, 551, 57-61.
34. Perlovich, G. L.; Hansen, L. K.; Volkova, T. V.; Mirza, S.; Manin, A. N.; Bauer-Brandl, A. Thermodynamic and structural aspects of hydrated and unhydrated phases of 4-hydroxybenzamide. Cryst. Growth Des. 2007, 7, 2643-2648.
35. Volkova, T. V.; Blokhina, S. V.; Ryzhakov, A. M.; Sharapova, A. V.; Ol'khovich, M. V.; Perlovich, G. L. Vapor pressure and sublimation thermodynamics of aminobenzoic acid, nicotinic acid, and related amido-derivatives. J. Therm. Anal. Calorim. 2016, 123, 841-849.
36. Cox, J. D.; Wagman, D. D.; Medvedev, V. A. CODATA key values for thermodynamics; Hemisphere Pub. Corp.: New York, 1989.
37. Olofsson, G. Assignment of Uncertainties. In Combustion calorimetry; Sunner, S., Månsson, M., Eds.; Pergamon Press: 1979; pp 137-159.
38. Wieser, M. E.; Holden, N.; Coplen, T. B.; Bohlke, J. K.; Berglund, M.; Brand, W. A.; De Bievre, P.; Groning, M.; Loss, R. D.; Meija, J.; Hirata, T.; Prohaska, T.; Schoenberg, R.; O'Connor, G.; Walczyk, T.; Yoneda, S.; Zhu, X. K. Atomic weights of the elements 2011 (IUPAC technical report). Pure Appl. Chem. 2013, 85, 1047-1078.
39. Anderson, C. M.; Gilbert, E. C. The apparent energy of the N-N bond as calculated from heats of combustion. J. Am. Chem. Soc. 1942, 64, 2369-2372.
40. Cole, L. G.; Gilbert, E. C. The heats of combustion of some nitrogen compounds and the apparent energy of the N-N bond. J. Am. Chem. Soc. 1951, 73, 5423-5427.
41. Nurachmetov, N. N.; Beremzhanov, B. A.; Abramova, G. V.; Lebedev, B. V. Thermodynamics of (thio)amides and their compounds with mineral acids at (0-330)K. Thermochim. Acta 1985, 92, 329-332.
42. Kulagina, T. G.; Kiparisova, E. G. Enthalpies of combustion and of formation of derivatives of carbamide. Russ. J. Phys. Chem. (Engl. Transl.) 1987, 61, 261-262.
43. Steele, W. V.; Chirico, R. D.; Nguyen, A.; Hossenlopp, I. A.; Smith, N. K. Determination of ideal-gas enthalpies of formation for key compounds. AIChE Symp. Ser. 1990, 138-154.
44. Emel'yanenko, V. N.; Zaitseva, K. V.; Nagrimanov, R. N.; Solomonov, B. N.; Verevkin, S. P. Benchmark Thermodynamic Properties of Methyl- and Methoxy-Benzamides: Comprehensive Experimental and Theoretical Study. J. Phys. Chem. A 2016, 120, 8419-8429.
45. Hamilton, W. S.; Witt, L. C. Heat of combustion of isophthalamide. J. Chem. Eng. Data 1971, 16, 234-235.
46. Hamilton, W. S.; Witt, L. C. Heat of combustion of terephthalamide. J. Chem. Eng. Data 1972, 17, 138-139.
47. Suntsova, M. A.; Dorofeeva, O. V. Use of G4 Theory for the Assessment of Inaccuracies in Experimental Enthalpies of Formation of Aromatic Nitro Compounds. J. Chem. Eng. Data 2016, 61, 313-329.
48. Acree, W. E. Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation. Thermochim. Acta 1991, 189, 37-56.
49. Brittain, H. G. Vibrational Spectroscopic Studies of Cocrystals and Salts. 1. The Benzamide-Benzoic Acid System. Cryst. Growth Des. 2009, 9, 2492-2499.
50. Perlovich, G. L.; Volkova, T. V.; Bauer-Brandl, A. Towards an understanding of the molecular mechanism of solvation of drug molecules: a thermodynamic approach by crystal lattice energy, sublimation, and solubility exemplified by paracetamol, acetanilide, and phenacetin. J. Pharm. Sci. 2006, 95, 2158-2169.
51. Salmon, A.; Dalmazzone, D. Prediction of Enthalpy of Formation in the Solid State (at 298.15K) using Second-Order Group Contributions. Part 1. Carbon-Hydrogen and Carbon-Hydrogen-Oxygen Compounds. J. Phys. Chem. Ref. Data 2006, 35, 1443-1457.
52. Andon, R. J. L.; Biddiscombe, D. P.; Cox, J. D.; Handley, R.; Harrop, D.; Herington, E. F. G.; Martin, J. F. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols. J. Chem. Soc. 1960, 5246-5254.
53. Roux, M. V.; Temprado, M.; Chickos, J. S.; Nagano, Y. Critically evaluated thermochemical properties of polycyclic aromatic hydrocarbons. J. Phys. Chem. Ref. Data 2008, 37, 1855-1996.
54. Aarset, K.; Page, E. M.; Rice, D. A. Hydrogen Bonding in the Gas-Phase: The Molecular Structures of 2-Hydroxybenzamide (C7H7NO2) and 2-Methoxybenzamide (C8H9NO2), Obtained by Gas-Phase Electron Diffraction and Theoretical Calculations. J. Phys. Chem. A 2013, 117, 3034-3040.
55. Pinto, S. S.; Diogo, H. P.; Guedes, R. C.; Costa Cabral, B. J.; Minas da Piedade, M. E.; Martinho Simões, J. A. Energetics of Hydroxybenzoic Acids and of the Corresponding Carboxyphenoxyl Radicals. Intramolecular Hydrogen Bonding in 2-Hydroxybenzoic Acid. J. Phys. Chem. A 2005, 109, 9700-9708.
56. Huque, F. T. T.; Platts, J. A. The effect of intramolecular interactions on hydrogen bond acidity. Org. Biomol. Chem. 2003, 1, 1419-1424.
57. Jeffrey, G. A. An Introduction to Hydrogen Bonding, Topics in Physical Chemistry; Oxford University Press: 1997).
58. Allinger, N. L.; Yuh, Y. H.; Lii, J. H. Molecular mechanics. The MM3 force field for hydrocarbons. J. Am. Chem. Soc. 1989, 111, 8551-8566.