Regioselectivity of the Pauson-Khand reaction in single-walled carbon nanotubes

Juan Pablo Martínez*, María Vizuete, Luis M. Arellano, Albert Poater, F. Matthias Bickelhaupt, Fernando Langa, Miquel Solà

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review


Chemical functionalization of nanotubes, in which their properties can be combined with those of other classes of materials, is fundamental to improve the physicochemical properties of nanotubes for potential technological applications. In this work, we theoretically and experimentally examine the Pauson-Khand reaction (PKR) on zig-zag, armchair, and chiral single-walled carbon nanotubes (SWCNTs). Our benchmarked density functional theory (DFT) calculations show that an alternative pathway to the widely accepted Magnus reaction pathway has significantly lower energy barriers, thus suggesting the use of this alternative pathway to predict whether a PKR on SWCNTs is favored or hampered. Accessible energy barriers of up to 16 kcal mol−1 are estimated and our results suggest that semiconducting SWCNTs react faster than metallic ones, although both types can be functionalized. Guided by our theoretical predictions, cyclopentenones are successfully attached to SWCNTs by heating and are, subsequently, characterized in the laboratory.

Original languageEnglish
Pages (from-to)15078-15089
Number of pages12
Issue number31
Early online date25 Jul 2018
Publication statusPublished - 21 Aug 2018


Excellent service by the Stichting Academisch Rekencentrum Amsterdam (SARA) and the Consorci de Serveis Universitaris de Catalunya (CSUC) is gratefully acknowledged. A. P. and F. L. thank the Spanish MINECO for projects CTQ2014-59832-JIN and CTQ2016-79189-R, respectively. M. S. thanks EU for a FEDER fund (UNGI08-4E-003), the Generalitat de Catalunya for project 2017SGR39, the Xarxa de Referència en Química Teòrica I Computacional, and ICREA Academia 2014 prize, and MINECO of Spain through project CTQ2017-85341-P. M. V. thanks CYTEMA-SANTANDER for a postdoctoral grant and L. M. A. thanks the Spanish MINECO for a FPI grant.

FundersFunder number
European Commission
Generalitat de Catalunya2017SGR39
Ministerio de Economía y CompetitividadCTQ2017-85341-P
Institució Catalana de Recerca i Estudis Avançats
European Regional Development FundUNGI08-4E-003


    Dive into the research topics of 'Regioselectivity of the Pauson-Khand reaction in single-walled carbon nanotubes'. Together they form a unique fingerprint.

    Cite this