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At a temperature of 70\u00b0C, the pterin alkylation regioselectively favored the O4 over the N3. The O4 was also favored when using solvents, in which the reactants had increased solubility, namely <jats:italic>N,N<\/jats:italic>\u2010dimethylformamide and <jats:italic>N,N<\/jats:italic>\u2010dimethylacetamide, rather than solvents in which the reactants had very low solubility (tetrahydrofuran and dichloromethane). Density functional theory (<jats:styled-content style=\"fixed-case\">DFT<\/jats:styled-content>) computed enthalpies correlate to regioselectivity being kinetically driven because the less stable O\u2010isomer forms in higher yield than the more stable N\u2010isomer. Once formed these compounds did not interconvert thermally or undergo a unimolecular \u201cwalk\u201d rearrangement. Mechanistic rationale for the factors underlying the regioselective alkylation of pterins is suggested, where kinetic rather than thermodynamic factors are key in the higher yield of the <jats:italic>O<\/jats:italic>\u2010isomer. Computations also predicted greater solubility and reduced triplet state energetics thereby improving the properties of the alkylated pterins as <jats:sup>1<\/jats:sup>O<jats:sub>2<\/jats:sub> sensitizers. Insight on thermal and photostability of the alkylated pterins is also provided.<\/jats:p>","DOI":"10.1111\/php.12905","type":"journal-article","created":{"date-parts":[[2018,2,13]],"date-time":"2018-02-13T15:47:43Z","timestamp":1518536863000},"page":"834-844","source":"Crossref","is-referenced-by-count":6,"title":["Kinetic Control in the Regioselective Alkylation of Pterin Sensitizers: A Synthetic, Photochemical, and Theoretical Study"],"prefix":"10.1111","volume":"94","author":[{"given":"Niluksha","family":"Walalawela","sequence":"first","affiliation":[{"name":"Department of Chemistry Brooklyn College City University of New York Brooklyn NY"},{"name":"Ph.D. Program in Chemistry The Graduate Center of the City University of New York New York NY"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mariana","family":"Vignoni","sequence":"additional","affiliation":[{"name":"Department of Chemistry Brooklyn College City University of New York Brooklyn NY"},{"name":"Instituto de Investigaciones Fisicoqu\u00edmicas Te\u00f3ricas y Aplicadas (INIFTA) Departamento de Qu\u00edmica Facultad de Ciencias Exactas Universidad Nacional de La Plata (UNLP) CCT La Plata\u2010CONICET La Plata Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda Noel","family":"Urrutia","sequence":"additional","affiliation":[{"name":"Instituto de Investigaciones Fisicoqu\u00edmicas Te\u00f3ricas y Aplicadas (INIFTA) Departamento de Qu\u00edmica Facultad de Ciencias Exactas Universidad Nacional de La Plata (UNLP) CCT La Plata\u2010CONICET La Plata Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sarah J.","family":"Belh","sequence":"additional","affiliation":[{"name":"Department of Chemistry Brooklyn College City University of New York Brooklyn NY"},{"name":"Ph.D. Program in Chemistry The Graduate Center of the City University of New York New York NY"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Edyta M.","family":"Greer","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences Baruch College City University of New York New York NY"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andr\u00e9s H.","family":"Thomas","sequence":"additional","affiliation":[{"name":"Instituto de Investigaciones Fisicoqu\u00edmicas Te\u00f3ricas y Aplicadas (INIFTA) Departamento de Qu\u00edmica Facultad de Ciencias Exactas Universidad Nacional de La Plata (UNLP) CCT La Plata\u2010CONICET La Plata Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander","family":"Greer","sequence":"additional","affiliation":[{"name":"Department of Chemistry Brooklyn College City University of New York Brooklyn NY"},{"name":"Ph.D. Program in Chemistry The Graduate Center of the City University of New York New York NY"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,3,15]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ00739F"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2016.04.196"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.6b00420"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamem.2015.11.002"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar050151c"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200390025"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703743"},{"key":"e_1_2_6_9_1","article-title":"Lipophilic decyl chain\u2010pterin conjugates with sensitizer properties","author":"Vignoni M.","year":"2017","journal-title":"Mol. 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