caa a22 4500 606182306 CHVBK 20210128100815.0 cr unu---uuuuu 210128e20150301xx s 000 0 eng 10.1007/s10876-014-0827-9 doi (NATIONALLICENCE)springer-10.1007/s10876-014-0827-9 1,3-Dipolar Cycloaddition in Stone-Wales Defective Carbon Nanotubes: A Computational Study [Elektronische Daten] [Fereshteh Naderi, Reza Ghafouri, Fatemeh Ektefa] We have theoretically investigated the [2+3] cycloaddition reactions of 1,3 dipoles, azides (N≡N+-NR−), with Stone-Wales (SW) defective (n, n) single-walled carbon nanotubes (SWCNTs), n=4, 5, and 6. It is shown that topological defects such as the SW defects could drastically change the electronic structure and chemical reactivity of SWCNTs. Among the functionalized SW defective SWCNTs, the most stable configurations are obtained when the 1,3-dipoles are close to the heptagon-heptagon C=C bonds of SW defects. Therefore, azide derivatives N≡N+-NR−, R=-H,-CH3,-NH2, -Ph, and -CN, are put close to the heptagon-heptagon C=C bonds of the SWCNTs. Negative values obtained for 1,3-dipolar cycloaddition reaction energies Er indicate the exothermic character of [2+3] cycloaddition reactions. The results also indicate that the orientations of SW defects at the sidewalls of the SWCNTs (diagonal or parallel to the tube axis) play an important role in the reactivity of the C=C double bonds of SW defects. Substitution of an electron donating functional for hydrogen atom of azide leads to a decrease in the energy difference between the E HOMO of the dipole and the E LUMO of the dipolarophile, which facilitates interaction between the substrate (C=C bonds) and 1,3 dipoles. Springer Science+Business Media New York, 2014 [2+3] Cycloadditions nationallicence 1,3 Dipole nationallicence Stone-Wales defect nationallicence DFT nationallicence Naderi Fereshteh Department of Chemistry, Shahr -e- Qods branch, Islamic Azad University, Shahr -e- Qods, Tehran, Iran aut Ghafouri Reza Department of Chemistry, Yadegar -e- Imam Khomeini (RAH) Branch, Islamic Azad University, Tehran, Iran aut Ektefa Fatemeh Department of Chemistry, Yadegar -e- Imam Khomeini (RAH) Branch, Islamic Azad University, Tehran, Iran aut Journal of Cluster Science Springer US; http://www.springer-ny.com 26/2(2015-03-01), 581-594 1040-7278 26:2<581 2015 26 10876 https://doi.org/10.1007/s10876-014-0827-9 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s10876-014-0827-9 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Naderi Fereshteh Department of Chemistry, Shahr -e- Qods branch, Islamic Azad University, Shahr -e- Qods, Tehran, Iran aut NATIONALLICENCE 700 1- Ghafouri Reza Department of Chemistry, Yadegar -e- Imam Khomeini (RAH) Branch, Islamic Azad University, Tehran, Iran aut NATIONALLICENCE 700 1- Ektefa Fatemeh Department of Chemistry, Yadegar -e- Imam Khomeini (RAH) Branch, Islamic Azad University, Tehran, Iran aut NATIONALLICENCE 773 0- Journal of Cluster Science Springer US; http://www.springer-ny.com 26/2(2015-03-01), 581-594 1040-7278 26:2<581 2015 26 10876