Molecular mechanism of Diels–Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene: B3LYP/6-31G(d) computational study

Radomir JASINSKI; Andrzej BARANSKI

doi:https://doi.org/10.3906/kim-1208-13

Makale detayları

Molecular mechanism of Diels–Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene: B3LYP/6-31G(d) computational study

Yazarlar:

Radomir JASINSKI | Andrzej BARANSKI

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2013 Vol.37 Issue 5, pp.848-852

Belge Tipi:

Makale

Yayın Tarihi:

4/2013

Belge Dili:

İngilizce

Document ID (Org No.):

2000727355

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1208-13

Özet:

 

Analysis of reactivity indexes supports the polar character of   the reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene.  This is confirmed by the analysis of electronic properties of transition  complexes involved in the reaction paths using the B3LYP/6-31G(d) algorithm.  The transition state's asymmetry is large, but it is insufficient to provoke a   zwitterionic reaction mechanism. Attempts to find a heterocyclic   intermediate 7 in the reaction path ultimately leading to   5-endo-nitro-6-exo-trichloromethylnorbornene 3 have been unsuccessful.

 

Analysis of reactivity indexes supports the polar character of   the reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene.  This is confirmed by the analysis of electronic properties of transition  complexes involved in the reaction paths using the B3LYP/6-31G(d) algorithm.  The transition state's asymmetry is large, but it is insufficient to provoke a   zwitterionic reaction mechanism. Attempts to find a heterocyclic   intermediate 7 in the reaction path ultimately leading to   5-endo-nitro-6-exo-trichloromethylnorbornene 3 have been unsuccessful.

Makale detayları

Molecular mechanism of Diels–Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene: B3LYP/6-31G(d) computational study

Yazarlar: Radomir JASINSKI | Andrzej BARANSKI

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2013 Vol.37 Issue 5, pp.848-852

Belge Tipi: Makale

Yayın Tarihi: 4/2013

Belge Dili: İngilizce

Document ID (Org No.): 2000727355

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/kim-1208-13

Sayı

Yazarlar:

Radomir JASINSKI | Andrzej BARANSKI

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2013 Vol.37 Issue 5, pp.848-852

Belge Tipi:

Makale

Yayın Tarihi:

4/2013

Belge Dili:

İngilizce

Document ID (Org No.):

2000727355

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1208-13