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Pregled bibliografske jedinice broj: 976214

Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases


Saadat, Kayvan; Shiri, Ali; Kovačević, Borislav
Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases // New Journal of Chemistry, 42 (2018), 17; 14568-14575 doi:10.1039/c8nj02349b (međunarodna recenzija, članak, znanstveni)


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Naslov
Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases

Autori
Saadat, Kayvan ; Shiri, Ali ; Kovačević, Borislav

Izvornik
New Journal of Chemistry (1144-0546) 42 (2018), 17; 14568-14575

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

Ključne riječi
neutral organic superbases ; troponimines ; proton affinity ; pKa values

Sažetak
In the present study, N-methyl-2, 4, 6- cycloheptatriene-1-imine (Troponimine) with (Me)2N- and MeO- substituents have been investigated theoretically to evaluate their suitability as a new neutral organic superbase. To introduce the aforementioned system, thermochemical parameters such as gas basicity and proton affinity have been calculated along with their pKBH+ values in acetonitrile. Results revealed that all studied troponimine derivatives are more basic than 1, 8- bis(dimethylamino)-naphthalene whose gas phase basicity of 237 kcal mol-1 is considered to be the borderline between ordinary bases and superbases. However, the most important finding is that some of the proposed troponeimines are much stronger bases than the well-established cyclopropenimine superbases. Origin of troponimine basicity is elucidated through NICS calculations which reveal that troponimines become aromatic upon protonation. AIM analyses revealed that the hydrogen bond could also contribute to the basicity if a suitable substituent is located on the adjacent of the imine group of the troponimine.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Borislav Kovačević (autor)

Citiraj ovu publikaciju

Saadat, Kayvan; Shiri, Ali; Kovačević, Borislav
Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases // New Journal of Chemistry, 42 (2018), 17; 14568-14575 doi:10.1039/c8nj02349b (međunarodna recenzija, članak, znanstveni)
Saadat, K., Shiri, A. & Kovačević, B. (2018) Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases. New Journal of Chemistry, 42 (17), 14568-14575 doi:10.1039/c8nj02349b.
@article{article, year = {2018}, pages = {14568-14575}, DOI = {10.1039/c8nj02349b}, keywords = {neutral organic superbases, troponimines, proton affinity, pKa values}, journal = {New Journal of Chemistry}, doi = {10.1039/c8nj02349b}, volume = {42}, number = {17}, issn = {1144-0546}, title = {Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases}, keyword = {neutral organic superbases, troponimines, proton affinity, pKa values} }
@article{article, year = {2018}, pages = {14568-14575}, DOI = {10.1039/c8nj02349b}, keywords = {neutral organic superbases, troponimines, proton affinity, pKa values}, journal = {New Journal of Chemistry}, doi = {10.1039/c8nj02349b}, volume = {42}, number = {17}, issn = {1144-0546}, title = {Substituted troponimines: when aromatization of the conjugate acid leads to very strong neutral organic superbases}, keyword = {neutral organic superbases, troponimines, proton affinity, pKa values} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • Arts & Humanities Citation Index (A&HCI)
  • Scopus


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