Skip to main content
SpringerLink
Log in

Thermochemical and structural study of a dibenzocycloheptane cyanoenamine

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The crystalline and gas phase enthalpy of formation of 5-cyano-7H-dibenzo-[a,c]-cyclohepten-6-amine (1) (142.0 ± 11.6 and 264 ± 20 kJ mol−1, respectively) are reported. The sublimation enthalpy at T = 298.15 K for this compound was evaluated by combining the fusion enthalpy from DSC measurements adjusted to 298 K with estimated vaporization enthalpy. The experimental enthalpy of formation is discussed in relationship with values calculated at the G3(MP2)//B3LYP level of quantum chemical theory and by means of group additivity. The crystal structure of this compound was determined by X-ray crystallography and shown to exist entirely in the cyanoenamine form 1, i.e. not the tautomeric α-cyanoimine 2.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. St Perisanu, Banciu A, Banciu MD (1993) Thermochim Acta 228:393–396

    Article  Google Scholar 

  2. St Perisanu, Banciu MD (1998) Thermochim Acta 320:9–12

    Article  Google Scholar 

  3. St Perisanu, Contineanu I, Banciu MD, Liebman JF, Farivar BS, Buckheit MA, Chickos JS, Rath N, Hillesheim D (2003) Thermochim Acta 400:109–120

    Article  Google Scholar 

  4. St Perisanu, Contineanu I, Banciu MD, Neacsu A, Chivu L (2005) Rev Chim (Bucuresti) 56:813–816

    Google Scholar 

  5. St Perisanu, Contineanu I, Banciu MD, Zhan H, Rath N, Chickos JS (2006) Struct Chem 17:639–648

    Article  Google Scholar 

  6. Miranda MS, Morais VMF, Matos MAR, Liebman JF (2010) J Chem Thermodyn 42:1094–1100

    Article  CAS  Google Scholar 

  7. St Perisanu, Contineanu I, Neacsu A, Notario R, Roux MV, Liebman JF, Dodson BJ (2011) Struct Chem 22:89–94

    Article  Google Scholar 

  8. Miranda MS, Matos MAR, Morais VMF, Liebman JF (2011) J Chem Thermodyn 43:364–370

    Article  CAS  Google Scholar 

  9. Rogers DW, Pododensin A, Liebman JF (1993) J Org Chem 58:2589–2592

    Article  CAS  Google Scholar 

  10. Matos MAR, Miranda MS, Pinto NAB, Morais VMF, Dhananjaya N, Liebman JF (2005) Mol Phys 103:1885–1894

    Article  CAS  Google Scholar 

  11. Edwards KF, Perisanu St, Liebman JF (2013) Int J Chem Model 5:51–65

    CAS  Google Scholar 

  12. Temprado M, Roux MV, Umnahanant P, Zhao H, Chickos JS (2005) J Phys Chem B 109:12590–12595

    Article  CAS  Google Scholar 

  13. Liebman JF, Perks HM (1994) In: Rappoport Z (ed) The chemistry of enamines. Wiley, Chichester

    Google Scholar 

  14. Verevkin SP, Morgenthaler J, Rüchardt C (1997) J Chem Thermodyn 29:1175–1183

    Article  CAS  Google Scholar 

  15. Slayden SW, Liebman JF (1997) In: Patai S (ed) The chemistry of functional groups supplement A3: the chemistry of Doubly-bonded functional groups. Wiley, Chichester

    Google Scholar 

  16. Zăvoianu D, Perisanu St, Moga-Gheorghe S, Bornaz C (1983) Rev Chim (Bucuresti) 34:987–988

    Google Scholar 

  17. Zavoianu D, Contineanu I, Moga-Gheorghe S, Marchidan D (1986) Rev Chim (Bucuresti) 37:1055–1058

    CAS  Google Scholar 

  18. Lebedeva ND, Gutner NM (1972) Zhur Fiz Khim 46:1058–1059

    CAS  Google Scholar 

  19. Vasil’eva TF, Zhil’tsova EN, Dogonina MD (1981) Termodin Organ Soedin 1981:49–50

    Google Scholar 

  20. Nurullaev GG, Akhmedov RM, Karasharli KA, Mekhtiev SI (1982) Azerb Khim Zh 5:78–82

    Google Scholar 

  21. Welle FM, Verevkin SP, Beckhaus HD, Ruchardt C (1997) Liebigs Ann 1997:155–163

    Article  Google Scholar 

  22. Kenner J, Turner EG (1911) J Chem Soc Trans 99:2101–2114

    Article  CAS  Google Scholar 

  23. Nakazaki M (1951) Nippon Kagaku Zasshi 72:739–743

    Article  CAS  Google Scholar 

  24. Eistert B, Minas H (1964) Chem Ber 97:2479–2489

    Article  CAS  Google Scholar 

  25. Bergmann ED, Agranat I, Kraus MA (1967) J Org Chem 32:600–602

    Article  CAS  Google Scholar 

  26. Tolbert LM, Ali MZ (1982) J Org Chem 47:4793–4795

    Article  CAS  Google Scholar 

  27. Pedley JB (1994) Thermochemical data and structures of organic compounds, vol 1. TRC Data Series, College Station

    Google Scholar 

  28. Davis MA, Winthrop SO, Thomas RA, Herr F, Charest MP, Gaudry R (1964) J Med Chem 7:88–94

    Article  CAS  Google Scholar 

  29. Davis MA, Winthrop SO, Stewart W, Sinahara FA, Herr F (1963) J Med Chem 6:251–255

    Article  CAS  Google Scholar 

  30. Nossek D, Banciu MD (1977) Bul St IPB Ser Chim Metal 39:80–90

    Google Scholar 

  31. Banciu MD, Draghici C, Popescu A, Banciu A, Simion A (1998) Rev Roum Chim 43:651–662

    Google Scholar 

  32. Banciu MD, Parvulescu L, Banciu A, Simion A, Costea C, Draghici C, Pop M, Mihãiescu D (2001) J Anal Appl Pyrolysis 57:261–274

    Article  CAS  Google Scholar 

  33. Banciu MD, Costea C, Draghici C, Banciu A, Mihaiescu D, Ciuculescu D (2003) J Anal Appl Pyrolysis 67:359–368

    Article  CAS  Google Scholar 

  34. Gaussian 03, Revision E.01, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck, AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA, Gaussian, Inc., Wallingford CT, 2004

  35. Baboul A, Curtiss LA, Redfern PC, Raghavachari K (1999) J Chem Phys 110:7650–7657

    Article  CAS  Google Scholar 

  36. Anantharaman B, Melius CF (2005) J Phys Chem A 109:1734–1747

    Article  CAS  Google Scholar 

  37. Sheldrick GM (2008) Bruker analytical X-ray division, Madison, WI

  38. Sheldrick GM (2008) Acta Cryst A64:112–122

    Google Scholar 

  39. Marchidan DI, Telea C (1971) Studii Cerc Chim 3:283–293

    Google Scholar 

  40. Contineanu I, Telea C (1996) Romanian Patent Nr. 11

  41. Wagman DD, Evans WH, Parker VB, Schumm RH, Halow I, Bailey SM, Churney KL, Nuttall RL (1982) The NBS tables of chemical thermodynamic properties. Selected values for inorganic and C1 and C2 organic substances in SI units. J Phys Chem Ref Data 11(Suppl 2):1–392

    Google Scholar 

  42. Chickos JS (1998) Thermochim Acta 313:19–26

    Article  CAS  Google Scholar 

  43. Chickos JS, Hesse DG, Liebman JF (1993) Struct Chem 4:261–269

    Article  CAS  Google Scholar 

  44. Chickos JS, Acree WE Jr, Liebman JF (1998) In: Frurip DR, Irikura KK (eds) Computational thermochemistry, prediction and estimation of molecular thermodynamics. ACS Symposium Series 677. ACS, Washington DC

    Google Scholar 

  45. Roux MV, Temprado M, Chickos JS, Nagano Y (2008) J Phys Chem Ref Data 37:1855–1996

    Article  CAS  Google Scholar 

  46. Domalski ES, Hearing ED (1993) J Phys Chem Ref Data 22:805–1159

    Article  CAS  Google Scholar 

  47. Salmon A, Dalmazzone D (2007) J Phys Chem Ref Data 36:19–58

    Article  CAS  Google Scholar 

  48. Zăvoianu D, Perisanu St, Moga-Gheorghe S, Bornaz C, Gaman V, Radulescu A (1982) Rev Chim (Bucureşti) 33:432–434

    Google Scholar 

  49. Zăvoianu D, Ciocazanu I, Moga-Gheorghe S, Cuza O, Bornaz C (1985) Rev Chim (Bucureşti) 36:220–222

    Google Scholar 

  50. Zăvoianu D, Ciocăzanu I (2003) Anal Univ Buc Chim XII (s.n.) 1:137–142

    Google Scholar 

  51. Zăvoianu D, Contineanu I, Moga-Gheorghe S, Bornaz C (1990) Rev Chimie (Bucureşti) 41:15–16

    Google Scholar 

  52. Ciocăzanu I, Zăvoianu D (1994) Rev Chimie (Bucureşti) 45:876–878

    Google Scholar 

  53. Verevkin SP (1998) Thermochim Acta 310:229–235

    Article  CAS  Google Scholar 

Download references

Acknowledgments

R. N. and J. F. L. gratefully acknowledge the support of the Spanish Ministerio de Economía y Competitividad under Project CTQ2010-16402.

Author information

Authors and Affiliations

  1. Department of General Chemistry, Polytechnic University of Bucharest, Str. Polizu nr. 1, Bucharest, Romania

    Stefan Perisanu

  2. Institute of Physical Chemistry of the Romanian Academy, Spl. Independentei 202, Bucharest, Romania

    Iulia Contineanu & Ana Neacsu

  3. Department of Chemistry and Biochemistry, University of Missouri – St. Louis, St. Louis, MO, 63121, USA

    Nigam P. Rath & James S. Chickos

  4. Instituto de Química Física ‘Rocasolano’, CSIC, Serrano 119, 28006, Madrid, Spain

    Rafael Notario

  5. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD, 21250, USA

    Joel F. Liebman

Authors
  1. Stefan Perisanu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Iulia Contineanu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ana Neacsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nigam P. Rath
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. James S. Chickos
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Rafael Notario
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Joel F. Liebman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Stefan Perisanu.

Additional information

This paper is dedicated to our coworker and friend Maria Victoria Roux.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Perisanu, S., Contineanu, I., Neacsu, A. et al. Thermochemical and structural study of a dibenzocycloheptane cyanoenamine. Struct Chem 24, 1975–1980 (2013). https://doi.org/10.1007/s11224-013-0286-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-013-0286-1

Keywords

Search

Navigation