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The charged analyte is transferred to the gas phase by electrospray. Diastereomeric complexes are formed with a volatile chiral selector in a buffer\u2010gas\u2010filled ion guide held at room temperature, mass\u2010selected, and subsequently spectrally differentiated by cryogenic ion trap vibrational spectroscopy. Based on the spectra of the pure complexes in a small diastereomer\u2010specific spectral range, the composition of diastereomeric mixtures is characterized using the cosine similarity score, from which the enantiomeric ratio in the solution is determined. The method is demonstrated for acidified alanine solutions and using three different chiral selectors (2\u2010butanol, 1\u2010phenylethanol, 1\u2010amino\u20102\u2010propanol). Among these, 2\u2010butanol is the best choice as a selector for protonated alanine, also because the formation ratio of the corresponding diastereomeric complexes is found to be independent of the nature of the enantiomer. Subsequently, a microfluidic chip is implemented to mix enantiomerically pure alanine solutions continuously and determine the enantiomeric ratio online with minimal sample consumption within one minute and with competitive accuracy.<\/jats:p>","DOI":"10.1002\/cphc.202300975","type":"journal-article","created":{"date-parts":[[2024,2,28]],"date-time":"2024-02-28T22:30:15Z","timestamp":1709159415000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Online\u2010Monitoring of the Enantiomeric Ratio in Microfluidic Chip Reactors Using Chiral Selector Ion Vibrational Spectroscopy"],"prefix":"10.1002","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1243-1142","authenticated-orcid":false,"given":"Sonja","family":"Schmahl","sequence":"first","affiliation":[{"name":"Wilhelm-Ostwald-Institut f\u00fcr Physikalische und Theoretische Chemie Universit\u00e4t Leipzig  Linn\u00e9stra\u00dfe 2 04103 Leipzig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7296-3549","authenticated-orcid":false,"given":"Francine","family":"Horn","sequence":"additional","affiliation":[{"name":"Wilhelm-Ostwald-Institut f\u00fcr Physikalische und Theoretische Chemie Universit\u00e4t Leipzig  Linn\u00e9stra\u00dfe 2 04103 Leipzig Germany"},{"name":"Fritz-Haber-Institut der Max-Planck-Gesellschaft  Faradayweg 4\u20136 14195 Berlin Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8738-2985","authenticated-orcid":false,"given":"Jiaye","family":"Jin","sequence":"additional","affiliation":[{"name":"Wilhelm-Ostwald-Institut f\u00fcr Physikalische und Theoretische Chemie Universit\u00e4t Leipzig  Linn\u00e9stra\u00dfe 2 04103 Leipzig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0417-7949","authenticated-orcid":false,"given":"Hannes","family":"Westphal","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Analytische Chemie Universit\u00e4t Leipzig  Linn\u00e9stra\u00dfe 3 04103 Leipzig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6295-8706","authenticated-orcid":false,"given":"Detlev","family":"Belder","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Analytische Chemie Universit\u00e4t Leipzig  Linn\u00e9stra\u00dfe 3 04103 Leipzig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6297-5856","authenticated-orcid":false,"given":"Knut R.","family":"Asmis","sequence":"additional","affiliation":[{"name":"Wilhelm-Ostwald-Institut f\u00fcr Physikalische und Theoretische Chemie Universit\u00e4t Leipzig  Linn\u00e9stra\u00dfe 2 04103 Leipzig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,3,19]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.watres.2017.08.003"},{"key":"e_1_2_8_2_1","unstructured":"\u00a0"},{"key":"e_1_2_8_3_2","volume-title":"Chiral Analysis. 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