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The key enablers for polymer informatics are machine-readable molecular string representations of the building blocks of a polymer, i.e., the monomers. In monomer strings, such as SMILES, symbols at the head and tail atoms indicate the locations of bond formation during polymerization. Since the linking of monomers determines a polymer\u2019s properties, the performance of AI prediction models will, ultimately, be limited by the accuracy of the head and tail assignments in the monomer SMILES. Considering the large number of polymer precursors available in chemical data bases, reliable methods for the automated assignment of head and tail atoms are needed. Here, we report a method for assigning head and tail atoms in monomer SMILES by analyzing the reactivity of their functional groups\u00a0based on\u00a0the atomic index of nucleophilicity. In a reference data set containing 206 polymer precursors, the HeadTailAssign (HTA) algorithm  correctly predicted the polymer class of 204 monomer SMILES,  achieving\u00a0an accuracy of 99%. The head and tail atoms were correctly assigned to 187 monomer SMILES, representing an accuracy of 91%. The HTA code is available for validation and reuse at\n                      <jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"https:\/\/github.com\/IBM\/HeadTailAssign\" ext-link-type=\"uri\">https:\/\/github.com\/IBM\/HeadTailAssign<\/jats:ext-link>\n                      .\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Scientific contribution<\/jats:title>\n                    <jats:p>The algorithm was successfully\u00a0applied to\u00a0data pre-processing by tagging the linkage bonds in monomers for defining the repeat units in polymerization reactions.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1186\/s13321-025-01098-x","type":"journal-article","created":{"date-parts":[[2025,10,28]],"date-time":"2025-10-28T13:49:55Z","timestamp":1761659395000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["HTA - An open-source software for assigning head and tail positions\u00a0to\u00a0monomer SMILES in polymerization reactions"],"prefix":"10.1186","volume":"17","author":[{"given":"Brenda","family":"de Souza Ferrari","sequence":"first","affiliation":[]},{"given":"Ronaldo","family":"Giro","sequence":"additional","affiliation":[]},{"given":"Mathias B.","family":"Steiner","sequence":"additional","affiliation":[]}],"member":"297","published-online":{"date-parts":[[2025,10,28]]},"reference":[{"issue":"1","key":"1098_CR1","doi-asserted-by":"publisher","DOI":"10.1088\/1757-899x\/1003\/1\/012135","volume":"1003","author":"MY Yuhazri","year":"2020","unstructured":"Yuhazri MY, Zulfikar AJ, Ginting A (2020) Fiber reinforced polymer composite as a strengthening of concrete structures: a review. 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