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A key element in these molecular tool compounds is the \u201celectrophilic trap\u201d that allows a covalent linkage with the target enzyme. The reactivity of this entity needs to be well balanced to effectively trap the desired enzyme, while not being attacked by off\u2010target nucleophiles. Here we investigate the intrinsic reactivity of substrates containing a class of widely used electrophilic traps, the three\u2010membered heterocycles with a nitrogen (aziridine), phosphorus (phosphirane), oxygen (epoxide) or sulfur atom (thiirane) as heteroatom. Using quantum chemical approaches, we studied the conformational flexibility and nucleophilic ring opening of a series of model substrates, in which these electrophilic traps are mounted on a cyclohexene scaffold (C<jats:sub>6<\/jats:sub>H<jats:sub>10<\/jats:sub>Y with Y=NH, PH, O, S). It was revealed that the activation energy of the ring opening does not necessarily follow the trend that is expected from C\u2212Y leaving\u2010group bond strength, but steeply decreases from Y=NH, to PH, to O, to S. We illustrate that the HOMO<jats:sub>Nu<\/jats:sub>\u2013LUMO<jats:sub>Substrate<\/jats:sub> interaction is an all\u2010important factor for the observed reactivity. In addition, we show that the activation energy of aziridines and phosphiranes can be tuned far below that of the corresponding epoxides and thiiranes by the addition of proper electron\u2010withdrawing ring substituents. Our results provide mechanistic insights to rationally tune the reactivity of this class of popular electrophilic traps and can guide the experimental design of covalent inhibitors and probes for enzymatic activity.<\/jats:p>","DOI":"10.1002\/chem.202201649","type":"journal-article","created":{"date-parts":[[2022,7,27]],"date-time":"2022-07-27T21:59:25Z","timestamp":1658959165000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Rational Tuning of the Reactivity of Three\u2010Membered Heterocycle Ring Openings via S<sub>N<\/sub>2 Reactions"],"prefix":"10.1002","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6291-1569","authenticated-orcid":false,"given":"Thomas","family":"Hansen","sequence":"first","affiliation":[{"name":"Departament de Qu\u00edmica Inorg\u00e0nica i Org\u00e0nica (Secci\u00f3 de Qu\u00edmica Org\u00e0nica) &amp; Institut de Qu\u00edmica Te\u00f2rica i Computacional (IQTCUB) Universitat de Barcelona  08028 Barcelona Spain"},{"name":"Department of Theoretical Chemistry Amsterdam Institute of Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale Modeling (ACMM) Vrije Universiteit Amsterdam  De Boelelaan 1083 1081 HV Amsterdam (The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8670-9031","authenticated-orcid":false,"given":"Alba","family":"Nin\u2010Hill","sequence":"additional","affiliation":[{"name":"Departament de Qu\u00edmica Inorg\u00e0nica i Org\u00e0nica (Secci\u00f3 de Qu\u00edmica Org\u00e0nica) &amp; Institut de Qu\u00edmica Te\u00f2rica i Computacional (IQTCUB) Universitat de Barcelona  08028 Barcelona Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3531-2138","authenticated-orcid":false,"given":"Jeroen D. 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