A DFT study of endocyclic allenes: unprecedentedly superbasic hydrocarbons

Antol, Ivana; Margetić, Davor (2016) A DFT study of endocyclic allenes: unprecedentedly superbasic hydrocarbons. New journal of chemistry, 40 (10). pp. 8191-8193. ISSN 1144-0546

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Official URL: http://pubs.rsc.org/en/content/articlehtml/2016/NJ...

Abstract

Density functional theory (DFT) calculations using the B3LYP, M05-2X and M06-2X functionals were employed in the study of basicity of allenes incorporated in seven-membered rings. These highly unstable species upon protonation give thermodynamically very stable tropylium cations, which are the origin of their extremely high basicity. An endocyclic allene → tropylium cation sequence was used for the design of novel hydrocarbon superbases, with calculated gas phase proton affinities exceeding well above 300 kcal mol−1.

Item Type:

Article

Uncontrolled Keywords:

Superbases ; tropylium cation ; DFT calculations

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects:

Project title	Project leader	Project code	Project type
Organski i bioorganski procesi u osnovnom i elektronski pobuđenim stanjima-	Mirjana Maksić	098-0982933-2920	MZOS
Host-guest međudjelovanja u policikličkim sustavima-	Davor Margetić	098-0982933-3218	MZOS

Depositing User:

Davor Margetić

Date Deposited:

17 May 2017 14:30

URI:

http://fulir.irb.hr/id/eprint/3484

DOI:

10.1039/C6NJ00623J