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Pregled bibliografske jedinice broj: 152310

On the origin of Baeyer strain in molecules - an ab initio and DFT analysis


Barić, Danijela; Maksić, Zvonimir
On the origin of Baeyer strain in molecules - an ab initio and DFT analysis // Theoretical chemistry accounts, 114 (2005), 1-3; 222-228 (međunarodna recenzija, članak, znanstveni)


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Naslov
On the origin of Baeyer strain in molecules - an ab initio and DFT analysis

Autori
Barić, Danijela ; Maksić, Zvonimir

Izvornik
Theoretical chemistry accounts (1432-881X) 114 (2005), 1-3; 222-228

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Strained ring; Angular strain; Baeyer strain; Bond bending

Sažetak
It is shown that destabilization energy of organic molecules containing small rings can be estimated by quasi homodesmotic reactions involving acyclic "strain-free" counterparts. These destabilization energies E-S can be well reproduced at the HF level employing cc-pVTZ basis set, because the contributions of the electron correlation and ZPV energy practically cancel each other in most cases. A predominating factor leading to a decreased stability of molecules involving small ring fragments is given by the Omega bond bending or Baeyer strain. It leads to a dramatic decrease in the electron-nuclei attraction, which is a hallmark of the angular strain. Similar results are obtained by the DFT-B3LYP method. It is strongly pointed out that Baeyer strain cannot be singled out from the total destabilization energy in a precise quantitative way, since it is interlocked with other types of intramolecular interactions like the nonbonded repulsions, a significant increase in the stability of the CH bonds emanating from the small cyclic structures and by the sigma-aromaticity or sigma-antiaromaticity in three- and four-membered rings, respectively. Nevertheless, it is fair to say that Baeyer strain is the essential factor in determining decreased stability of small ring compounds and that the diminished electron nuclear attraction is its characteristic signature at the global level.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
0098058

Ustanove
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Zvonimir Maksić (autor)

Avatar Url Danijela Barić (autor)

Citiraj ovu publikaciju

Barić, Danijela; Maksić, Zvonimir
On the origin of Baeyer strain in molecules - an ab initio and DFT analysis // Theoretical chemistry accounts, 114 (2005), 1-3; 222-228 (međunarodna recenzija, članak, znanstveni)
Barić, D. & Maksić, Z. (2005) On the origin of Baeyer strain in molecules - an ab initio and DFT analysis. Theoretical chemistry accounts, 114 (1-3), 222-228.
@article{article, year = {2005}, pages = {222-228}, keywords = {Strained ring, Angular strain, Baeyer strain, Bond bending}, journal = {Theoretical chemistry accounts}, volume = {114}, number = {1-3}, issn = {1432-881X}, title = {On the origin of Baeyer strain in molecules - an ab initio and DFT analysis}, keyword = {Strained ring, Angular strain, Baeyer strain, Bond bending} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus