Silaphenolates and Silaphenylthiolates: Two Unexplored Unsaturated Silicon Compound Classes Influenced by Aromaticity

↓ Direkt till sidans innehåll
↓ Direkt till sidans sekundära innehåll (sidomenyn)

Sökning: WFRF:(Ottosson Henrik) > Silaphenolates and ...

Alvi, Muhammad RoufUppsala universitet,Institutionen för biokemi och organisk kemi (författare)

Silaphenolates and Silaphenylthiolates : Two Unexplored Unsaturated Silicon Compound Classes Influenced by Aromaticity

Artikel/kapitelEngelska2012

Förlag, utgivningsår, omfång ...

2012-01-02
MDPI AG,2012
printrdacarrier

Nummerbeteckningar

LIBRIS-ID:oai:DiVA.org:uu-166896
https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-166896URI
https://doi.org/10.3390/molecules17010369DOI

Kompletterande språkuppgifter

Språk:engelska
Sammanfattning på:engelska

Ingår i deldatabas

SwePubSwePub

Klassifikation

Ämneskategori:ref swepub-contenttype
Ämneskategori:art swepub-publicationtype

Anmärkningar

Monosilicon analogs of phenolates and phenylthiolates are studied by quantum chemical calculations. Three different silaphenolates and three different silaphenylthiolates are possible; the ortho-, meta-, and para-isomers. For the silaphenolates, the meta- isomer is the thermodynamically most stable, regardless if the substituent R at Si is H, t-Bu or SiMe3. However, with R = H and SiMe3 the energy differences between the three isomers are small, whereas with R = t-Bu the meta- isomer is similar to 5 kcal/mol more stable than the ortho- isomer. For the silaphenylthiolates the ortho- isomer is of lowest energy, although with R = H the ortho- and meta- isomers are isoenergetic. The calculated nucleus independent chemical shifts (NICS) indicate that the silaphenolates and silaphenylthiolates are influenced by aromaticity, but they are less aromatic than the parent silabenzene. The geometries and charge distributions suggest that all silaphenolates and silaphenylthiolates to substantial degrees are described by resonance structures with an exocyclic C=O double bond and a silapentadienyl anionic segment. Indeed, they resemble the all-carbon phenolate and phenylthiolate. Silaphenylthiolates are less bond alternate and have slightly more negative NICS values than analogous silaphenolates, suggesting that this compound class is a bit more aromatic. Dimerization of the silaphenolates and silaphenylthiolates is hampered due to intramolecular Coulomb repulsion in the dimers, and silaphenolates with a moderately bulky SiMe3 group as substituent at Si should prefer the monomeric form.

Ämnesord och genrebeteckningar

NATURVETENSKAP Kemi Organisk kemi hsv//swe
NATURAL SCIENCES Chemical Sciences Organic Chemistry hsv//eng
silicon
aromaticity
quantum chemical calculations

Biuppslag (personer, institutioner, konferenser, titlar ...)

Ottosson, HenrikUppsala universitet,Institutionen för biokemi och organisk kemi(Swepub:uu)heott255 (författare)
Uppsala universitetInstitutionen för biokemi och organisk kemi (creator_code:org_t)

Sammanhörande titlar

Ingår i:Molecules: MDPI AG17:1, s. 369-3891431-51571420-3049

Internetlänk

Hitta via bibliotek

Molecules (Sök värdpublikationen i LIBRIS)

Till lärosätets databas

Hitta mer i SwePub

Av författaren/redakt...: Alvi, Muhammad R ...; Ottosson, Henrik

Om ämnet

NATURVETENSKAP: NATURVETENSKAP; och Kemi; och Organisk kemi

Artiklar i publikationen: Molecules

Av lärosätet: Uppsala universitet

Sök utanför SwePub

Sök vidare i:: Google; Google Book Search; Google Scholar

Kungliga biblioteket hanterar dina personuppgifter i enlighet med EU:s dataskyddsförordning (2018), GDPR. Läs mer om hur det funkar här.
Så här hanterar KB dina uppgifter vid användning av denna tjänst.

LIBRIS.kb.se