Sökning: onr:"swepub:oai:DiVA.org:ri-57307" >
Cyclopropyl Group :
Cyclopropyl Group : An Excited-State Aromaticity Indicator?
-
- Ayub, Rabia (författare)
- Uppsala universitet,Institutionen för kemi - BMC,Molekylär biomimetik,Henrik Ottosson
-
- Papadakis, Raffaello (författare)
- Uppsala universitet,Institutionen för kemi - BMC,Molekylär biomimetik
-
- Jorner, Kjell (författare)
- Uppsala universitet,Institutionen för kemi - BMC,Molekylär biomimetik,uppsala university,Henrik Ottosson
-
visa fler...
-
- Zietz, Burkhard (författare)
- Uppsala universitet,Fysikalisk kemi
-
- Ottosson, Henrik (författare)
- Uppsala universitet,Institutionen för kemi - BMC,Molekylär biomimetik,uppsala university
-
visa färre...
-
(creator_code:org_t)
- 2017-09-01
- 2017
- Engelska.
-
Ingår i: Chemistry - A European Journal. - : Wiley-VCH Verlag. - 0947-6539 .- 1521-3765. ; 23:55, s. 13684-13695
- Relaterad länk:
-
https://urn.kb.se/re...
-
visa fler...
-
https://doi.org/10.1...
-
https://urn.kb.se/re...
-
https://urn.kb.se/re...
-
visa färre...
Abstract
Ämnesord
Stäng
- The cyclopropyl (cPr) group, which is a well-known probe for detecting radical character at atoms to which it is connected, is tested as an indicator for aromaticity in the first ππ* triplet and singlet excited states (T1 and S1). Baird's rule says that the π-electron counts for aromaticity and antiaromaticity in the T1 and S1 states are opposite to Hückel's rule in the ground state (S0). Our hypothesis is that the cPr group, as a result of Baird's rule, will remain closed when attached to an excited-state aromatic ring, enabling it to be used as an indicator to distinguish excited-state aromatic rings from excited-state antiaromatic and nonaromatic rings. Quantum chemical calculations and photoreactivity experiments support our hypothesis; calculated aromaticity indices reveal that openings of cPr substituents on [4n]annulenes ruin the excited-state aromaticity in energetically unfavorable processes. Yet, polycyclic compounds influenced by excited-state aromaticity (e.g., biphenylene), as well as 4nπ-electron heterocycles with two or more heteroatoms represent limitations.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- aromaticity
- density functional calculations
- electronic structures
- photochemistry
- small-ring compounds
- Aromatic compounds
- Aromatization
- Density functional theory
- Electronic structure
- Ground state
- Photochemical reactions
- Quantum chemistry
- Quantum theory
- Antiaromaticity
- Aromaticities
- Aromaticity indices
- Cyclopropyl group
- Polycyclic compounds
- Quantum chemical calculations
- Singlet excited state
- Small rings
- Excited states
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
Hitta via bibliotek
Till lärosätets databas