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Substituents R=N(CH<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>, NH<jats:sub>2<\/jats:sub>, CH<jats:sub>3<\/jats:sub>, OCH<jats:sub>3<\/jats:sub>, COCH<jats:sub>3<\/jats:sub>, Cl, F, COH, CN, and NO<jats:sub>2<\/jats:sub> were each placed ortho, meta, and para to the I. The depth of the \u03c3\u2010hole on I is deepened as R becomes more electron\u2010withdrawing which is reflected in a strengthening of the halogen bond, which varied between 3.3 and 5.5\u2005kcal\u2009mol<jats:sup>\u22121<\/jats:sup>. In most cases, the ortho placement yields the largest perturbation, followed by meta and then para, but this trend is not universal. Parallel to these substituent effects is a progressive lengthening of the covalent C\u2212I bond. Formation of the halogen bond reduces the NMR chemical shielding of all three nuclei directly involved in the C\u2212I\u22c5\u22c5N interaction. The deshielding of the electron donor N is most closely correlated with the strength of the bond, as is the coupling constant between I and N, so both have potential use as spectroscopic measures of halogen bond strength.<\/jats:p>","DOI":"10.1002\/cphc.202200011","type":"journal-article","created":{"date-parts":[[2022,1,31]],"date-time":"2022-01-31T10:18:25Z","timestamp":1643624305000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Influence of Substituents in the Benzene Ring on the Halogen Bond of Iodobenzene with Ammonia"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0793-0369","authenticated-orcid":false,"given":"Steve","family":"Scheiner","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Utah State University  Logan Utah 84322-0300 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sarah","family":"Hunter","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Utah State University  Logan Utah 84322-0300 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,2,11]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"crossref","unstructured":"C.\u2005B. 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