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The regioselectivity of these reactions cannot be rationalized on the basis of the electronic demands of the reactants or frontier molecular\u2010orbital theory. Therefore, we applied to this problem a quantitative formulation of the HSAB principle to this problem developed within density functional theory. Global and local reactivity indices were computed at B3LYP\/6\u2010311+G(d,p) level both in vacuo and in carbon tetrachloride (by the COSMO approach). The direction of charge transfer upon reactive encounter has been determined and the computed regioselectivity has been shown to be in good agreement with the experimental results. The relationship between computed and experimental data and how it is affected by the solvent have been discussed.<\/jats:p>","DOI":"10.1002\/chem.200204681","type":"journal-article","created":{"date-parts":[[2003,6,6]],"date-time":"2003-06-06T08:07:35Z","timestamp":1054886855000},"page":"2770-2774","source":"Crossref","is-referenced-by-count":60,"title":["Arylazide Cycloaddition to Methyl Propiolate: DFT\u2010Based Quantitative Prediction of Regioselectivity"],"prefix":"10.1002","volume":"9","author":[{"given":"Giorgio","family":"Molteni","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alessandro","family":"Ponti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2003,6,6]]},"reference":[{"key":"e_1_2_5_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/prac.18930480114"},{"key":"e_1_2_5_2_2","first-page":"1","volume-title":"1,3\u2010Dipolar Cycloaddition Chemistry, Vol. 1","author":"Huisgen R.","year":"1984"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00084a001"},{"key":"e_1_2_5_3_3","first-page":"621","volume-title":"1,3\u2010Dipolar Cycloaddition Chemistry, Vol. 1","author":"Lwowsky W.","year":"1984"},{"key":"e_1_2_5_3_4","volume-title":"The Chemistry of the Azido Group","year":"1971"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol010220x"},{"key":"e_1_2_5_4_3","doi-asserted-by":"publisher","DOI":"10.1021\/ol020096x"},{"key":"e_1_2_5_4_4","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020617)114:12<2214::AID-ANGE2214>3.0.CO;2-E"},{"key":"e_1_2_5_4_5","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO;2-7"},{"key":"e_1_2_5_4_6","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020617)114:12<2217::AID-ANGE2217>3.0.CO;2-X"},{"key":"e_1_2_5_4_7","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020617)41:12<2113::AID-ANIE2113>3.0.CO;2-Q"},{"key":"e_1_2_5_4_8","doi-asserted-by":"publisher","DOI":"10.1021\/ja0206644"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO;2-W"},{"key":"e_1_2_5_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1177\/095632029800900604"},{"key":"e_1_2_5_6_3","doi-asserted-by":"publisher","DOI":"10.1021\/jm00050a015"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm990373e"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(00)00422-4"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00803a017"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00803a018"},{"key":"e_1_2_5_11_2","volume-title":"Density Functional Theory of Atoms and Molecules","author":"Parr R. 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