2024-03-28T16:40:01Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1093802021-10-27T11:57:19Zcom_10261_81com_10261_5col_10261_334
2015-01-15T09:49:17Z
urn:hdl:10261/109380
A computational study on 3-azonia-,3-phosphonia-, and 3-arsoniaspiro [2.2] pentanes and related three-membered heterocycles
Trujillo, Cristina
Sánchez-Sanz, Goar
Alkorta, Ibon
Elguero, José
Pnicogens
Spiro compounds
Strained compounds
Density functional calculations
Aromaticity
A theoretical study at the ab initio MP2/6-311++G(d,p) level of theory is carried out to characterize several heterocyclic spiro-[2.2]pentane cations with N, P, and As as spiro atoms. The strain and relative stability of the spiropentanes are obtained through isodesmic reactions. Nucleus-independent chemical shifts (NICS) and 3D NICS isosurfaces show s-aromatic characteristics, similar to those found in cyclopropane. The interaction with the Cl- anion, which results in four different stationary structures, is studied and characterized by means of the atoms in molecules methodology, and Cl·pnicogen, Cl·H, and Cl·C interactions are found. The most stable structure in all cases corresponds to opening of one of the three-membered rings, due to the attack of the Cl atom, and C-Cl bond formation. Furthermore, the reaction with the 3-boranuidaspiro-[2.2]pentane anion results in the formation of a new compound through cleavage of one ring of both reactants.
2015-01-15T09:49:17Z
2015-01-15T09:49:17Z
2014
2015-01-15T09:49:17Z
artículo
Chemphyschem : a European journal of chemical physics and physical chemistry 15: 3493-3501 (2014)
http://hdl.handle.net/10261/109380
10.1002/cphc.201402442
eng
closedAccess
John Wiley & Sons