Strain effects in phenyl-substituted methanes. Geminal interaction between phenyl and the electron-releasing substituent in benzylamines and benzyl alcohols

Journal of Chemical and Engineering Data

Volumn 44, Issue 6, 1999, Pages 1245-1251

  Verevkin, Sergey P ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CALORIMETRY; ELECTRON TRANSPORT PROPERTIES; ELECTRONS; ENTHALPY; FREE RADICALS; METHANE; SUBSTITUTION REACTIONS; THERMAL EFFECTS; THERMODYNAMIC PROPERTIES; VAPOR PRESSURE; VAPORIZATION;

BENZYL ALCOHOLS; BENZYLAMINES; COMBUSTION CALORIMETRY; GEMINAL INTERACTION; GROUP CONTRIBUTION METHODOLOGY; PHENYL; STANDARD MOLAR ENTHALPIES OF VAPORIZATION;

AROMATIC HYDROCARBONS;

EID: 0033216491     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je990118z     Document Type: Article

References (39)

1. Ambrose, D.; Ghiassee, N. B. Vapour pressures, critical temperatures, and critical pressures of benzyl alcohol, octan-2-ol, and 2-ethylhexanl-ol. J. Chem. Thermodyn. 1990, 22, 307-311.
2. Atomic weights of the elements. Pure Appl Chem. 1994, 66, 2423-2444.
3. Beckhaus, H.-D. Force Field for the Calculation of Structure and Enthalpy of Formation of Alkylbenzenes. Chem. Ber. 1983, 116, 86-96.
4. Beckhaus, H.-D.; Kratt, G.; Lay, K.; Geiselmann, J.; Rüchardt, C.; Kitschke, B.; Lindner, H. J. 3,4-Dicyclohexyl-3,4-dimethylhexane-Enthalpy of Formation, Thermal Stability and Structure. Chem. Ber. 1980, 113, 3441-3455.
5. Beckhaus, H.-D.; Dogan, B.; Schaetzer, J.; Hellmann, S.; Rüchardt, C. Thermal Stability and Enthalpy of Formation of 1,1,2,2- and 1,1,1,2-Tetraphenylethane-Stabilising Energy of Benzhydryl- and Triphenylmethyl-Radicals. Chem. Ber. 1990, 123, 137-144.
6. Benson, S. W. Thermochemical Kinetics; Wiley: New York, 1976; p 274.
7. Carson, A. S.; Laye, P. G.; Yrekli, M. The enthalpy of formation of benzylamine. J. Chem. Thermodyn. 1977, 9, 827-829.
8. Chickos, J. S.; Hesse, D. G.; Panshin, S. Y.; Rogers, D. W.; Saunders, M.; Uffer, P. M.; Liebman, J. F. The strain energy of cyclotetradecane is small. J. Org. Chem. 1992, 57, 1897-1902.
9. Chickos, J. S.; Hesse, D. G.; Hosseini, S.; Liebman, J. F.; Mendenhall, G. D.; Verevkin, S. P.; Rakus, K.; Beckhaus, H.-D.; Rüchardt, C. Enthalpies of Vaporization of Some Highly Branched Hydrocarbons. J. Chem. Thermodyn. 1995, 27, 693-705.
10. CODATA Key Values for Thermodynamics; Cox, J. D., Wagman, D. D., Medvedev, V. A., Eds.; Hemisphere: New York, 1989.
11. Cubberley, A. H.; Mueller, M. B. Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol. J. Am. Chem. Soc. 1946, 68, 1149-1151.
12. Davis, W. M.; Heck, S. M.; Pritchard, H. O. Theoretical study of benzyl radical reactivity in combustion systems. J. Chem. Soc., Faraday Trans. 1998, 94, 2725-2728.
13. Hubbard, W. N.; Scott, D. W.; Waddington, G. In Experimental Thermochemistry; Rossini, F. D., Ed.; Interscience: New York, 1956; pp 75-127.
14. Landrieu, P.; Baylocq, F.; Johnson, J. R. Etude thermochimique dans la serie furanique. Bull. Soc. Chim. Fr. 1929, 45, 36-49.
15. Majer, V.; Svoboda, V. Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation; Blackwell Scientific Publications: Oxford, 1985; p 300.
16. Mathews, J. H. The accurate measurement of heats of vaporization of liquids. J. Am. Chem. Soc. 1926, 48, 562-576.
17. Miroshnichenko, E. A.; Orlov, Yu. D.; Korchatova, L. I.; Vorobeva, V. P.; Lebedev, Yu. A. Enthalpic Characteristic of Benzyldimethylamine. Zh. Phys. Khim. 1996, 70, 1583-1586.
18. Papina, T. S.; Pimenova, S. M.; Luk'yanova, V. A.; Kolesov, V. P. Standard enthalpies of formation of benzyl alcohol and α,α,α-trichlorotoluene. Russ. J. Phys. Chem. (Engl. Transl.) 1995, 69, 1951-1953; in original 2148.
19. Parks, G. S.; Manchester, K. E.; Vaughan, L. M. Heats of combustion and formation of some alcohols, phenols, and ketones. J. Chem. Phys. 1954, 22, 2089-2090.
20. Pedley, J. P.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986.
21. 2X compounds. Can. J. Chem. 1987, 65, 1845-1849.
22. Reid, R. C.; Prausnitz, J. M.; Sherwood, T. K. The Properties of Gases and Liquids, 3rd ed.; McGraw-Hill: New York, 1977; p 249.
23. Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Monteiro, M. F. B. M.; Gomes, M. L. A. C. N.; Chickos, J. S.; Smith, A. P.; Liebman, J. F. Thermochemical Studies for Determination of the Molar Enthalpy of Formation of Aniline Derivatives. Struct. Chem. 1996, 7, 367.
24. Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Gomes, M. L. A. C. N.; Johnson, M.; Pilcher, G. Enthalpies of combustion of din-propylamine, diisopropylamine, diisobutylamine, and di-sec-butylamine. J. Chem. Thermodyn. 1997, 29, 1025-1030.
25. Schaffer, F.; Verevkin, S. P.; Beckhaus, H.-D.; Rüchardt, C. Geminal Substituent Effects. 15. Enthalpies of Formation of a Series of Fluorinated Hydrocarbons and Strain-Free Group Increments to Assess Polar and Anomeric Stabilization and Strain. Liebigs Ann. I Recuel 1997, 1, 1333-1344.
26. Schleyer, P. v. R.; Williams, J. E.; Blanchard, K. B. The evaluation of strain in hydrocarbons. The strain in adamantane and its origin. J. Am. Chem. Soc. 1970, 92, 2377-2386.
27. Schmidlin, M. J. Recherches chimiques et thermochimiques sur la constitution des rosanilines. Ann. Chim. Phys. 1906, 1, 195-256.
28. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Tasker, I. R. Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine. J. Chem. Eng. Data 1996, 41, 1269-1284.
29. Van-Chin-Syan, Yu. Ya.; Dolbneva, T. N.; Dikii, M. A.; Cuchmarev, S. K. Thermochemistry of derivatives of isopropylbenzene and p-diisopropylbenzene. Russ. J. Phys. Chem. (Engl. Transl.) 1984, 58, 1783-1785.
30. Verevkin, S. P. Thermochemistry of amines. Experimental standard enthalpies of formation of some aliphatic and aromatic amines. J. Chem. Thermodyn. 1997a, 29, 891-899.
31. Verevkin, S. P. Thermochemistry of amines. Experimental standard enthalpies of formation of some aliphatic and aromatic amines. J. Chem, Thermodyn. 1997b, 29, 891-899.
32. Verevkin, S. P. Thermochemistry of Amines: Experimental Standard Molar Enthalpies of Formation of N-Alkylated Piperidines. Struct. Chem. 1998a, 9, 113-118.
33. Verevkin, S. P. Thermochemistry of Alcohols: Experimental Standard Molar Enthalpies of Formation and Strain of Some Alkyl and Phenyl Congested Alcohols. Struct. Chem. 1998c, 9, 375-382.
34. Verevkin, S. P. Thermochemical Properties of Branched Alkylsubstituted Benzenes. J. Chem. Thermodyn. 1998c, 30, 1029-1040.
35. Verevkin, S. P. Strain effects in phenyl substituted methanes. Geminal interactions between phenyl and electron-withdrawing cyano substituent in benzylcyanides. J. Chem. Thermodyn. 1999a, 31, accepted April 1999.
36. Verevkin, S. P. Strain effects in phenyl substituted methanes. Geminal interactions between phenyl and alkoxycarbonyl substituent. Thermochim. Acta 1999b 332, 27-32.
37. Verevkin, S. P.; Beckhaus, H.-D.; Rüchardt, C. Geminal Substituent Effects. 5. Enthalpies of Formation of Alkylsubstituted Malonic Acid and Aminocarboxylic Acid Esters. Thermochim. Acta 1992, 197, 27-39.
38. Verevkin, S.P., Beckhaus, H.-D., Schüle, U., Rüchardt, C. Experimental Enthalpies of Formation and Strain of the Methylated 1-Amino-2-Phenyl-Ethanes. Struct. Chem. 1998a, 9, 1-7.
39. Wirth, T. Neues zur Chemie stickstoffsubstituierter Radikale. Ph.D. Thesis, Freiburg, 1988.