{"id":32008,"date":"2026-09-14T14:51:36","date_gmt":"2026-09-14T13:51:36","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008"},"modified":"2026-09-14T15:04:25","modified_gmt":"2026-09-14T14:04:25","slug":"exploring-the-effect-that-causes-ring-size-specificity-of-transition-metals-for-polysulfide-dianions-cyclopentadienyl-26-di-isopropylphenoxy-titanium-pentasulfide","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008","title":{"rendered":"Exploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide."},"content":{"rendered":"
\n

In the previous post[1]<\/a><\/span> we described the orbital interactions involved in stabilising the formation of a Cp2<\/sub>TiS5<\/sub> complex (figure 1 below, X=S) rather than a Cp2<\/sub>TiS4<\/sub> complex when Cp2<\/sub>TiCl2<\/sub> is treated with a mixture of polysulfide dianions – and how these interactions can be “tuned” by variation in the ring atoms. <\/p>\n

\"\"<\/a>
\nFigure 1<\/strong>. Bis-cyclopentadienyl titanium sulfides.<\/p>\n

We identified[1]<\/a><\/span> one compound in which one of the Cp ligands itself is replaced by a hindered phenyoxy group (PUJFUV<\/a>[2]<\/a><\/span>) thus reducing the number of electrons the Cp ligand contributes to the valence shell of the Ti by four down to only two. Here the effect that this replacement has on the original orbital interactions is explored.<\/p>\n

A MN15L\/Def2-TZVPP calculation[3]<\/a><\/span> shows the geometry of PUJFUV (Figure 2) to have a calculated S-Ti bond length of 2.395 Å. This compares to 2.466Å for Cp2<\/sub>TiS5<\/sub> itself and this value is also significantly shorter than any of any of the other analogues described in the previous post (the shortest there being 1.453Å)[1]<\/a><\/span><\/p>\n

\"\"
\nFigure 2<\/strong>. The structure of PUJFUV, a cyclopentadienyl-2,6-di-isopropropoxy titanium pentasulfide.<\/p>\n

The interaction previously discussed[1]<\/a><\/span> involves overlap between a p-orbital like lone pair donor on a sufur attached to the Ti with an (almost) empty metal d-orbital (actually a Tid<\/sub>-Sp-π<\/sub> antibonding orbital) as acceptor. PUJFUV has four bonding electrons less than Cp2<\/sub>TiS5<\/sub> and hence formally now has three empty Ti d-orbitals rather than just one (although some of these electrons may become back-donated from O to Ti, see below).<\/p>\n

A pair of Sp<\/sub>-Tid<\/sub> interactions are now found,[4]<\/a><\/span> one from each sulfur to a different Ti d-orbital (Figures 2,3) with NBO E(2) interaction energies of 30.92 and 22.06 kcal\/mol (Figures 3 and 4 respectively). The first of these is significantly larger than the largest value previously found (23.59) by some margin[1]<\/a><\/span> whilst the second is about the same. For Cp2<\/sub>TiS5<\/sub> itself, only one such interaction was calculated – because there was only one unoccupied Ti d-orbital.<\/p>\n

\"\"
\nFigure 3<\/strong>. Sp<\/sub>-Tid<\/sub>z<\/sub>2 interaction 1, E(2) = 30.92.[4]<\/a><\/span><\/p>\n

\"\"
\nFigure 4<\/strong>. Sp<\/sub>-Tid<\/sub> interaction 2, E(2) = 22.06.[4]<\/a><\/span><\/p>\n

There are also three interactions between one of two lone pairs on the oxygen of the phenoxy group and a titanium d-orbital (Figures 5-7), two from a oxygen p-type lone pair (Figures 5 and 6) and one from an s-type oxygen lone pair (Figure 7). The three interactions conspire to reduce the length of the Ti-O bond to a short value, as noted previously, [1]<\/a><\/span> although this tendency towards a Ti≡O triple bond is only formal. <\/p>\n

\"\"
\nFigure 5<\/strong>. Op<\/sub>-Tid<\/sub> interaction 1, E(2) = 17.64.[4]<\/a><\/span><\/p>\n

\"\"
\nFigure 6<\/strong>. Op<\/sub>-Tid<\/sub> interaction 2, E(2) = 31.53.[4]<\/a><\/span><\/p>\n

\"\"
\nFigure 7<\/strong>. Os<\/sub>-Tid<\/sub> interaction 3, E(2) = 55.84.[4]<\/a><\/span><\/p>\n

The conclusion is that when a Cp ligand is replaced by an O-Ar one, formally three d-orbitals on the Ti rather than one become available for back-donation and the attached sulfur atoms on the sulfur ring can now interact more strongly with the Ti, hence shortening the Ti-S bond length and increasing the Ti-S partial double bond character. The back donation effect, noted[5]<\/a><\/span> as the crucial reason why 16-electron Ti complexes favour a ring with five rather than four sulfur atoms, is also increased in strength for this 12-electron version.This is likely to be the strongest such back-donation for TiS5<\/sub> systems, although the hunt is on for even stronger examples.<\/p>\n

References<\/h2>\n
  1. H. Rzepa, \"Identifying the origins of the ring-size specificity of transition metals for polysulfide anions: "tuning" the effect.\", 2026. https:\/\/doi.org\/10.59350\/p8zwp-39q65<\/a>\n\n<\/li>\n
  2. A.V. Firth, and D.W. Stephan, \"Monocyclopentadienyl\u2212Titanium Aryloxide Sulfide Complexes\", Inorganic Chemistry<\/i>, vol. 37, pp. 4726-4731, 1998. https:\/\/doi.org\/10.1021\/ic9800839<\/a>\n\n<\/li>\n
  3. H. Rzepa, \"PUJFUV\", 2026. https:\/\/doi.org\/10.5281\/zenodo.22690064<\/a>\n\n<\/li>\n
  4. H. Rzepa, \"PUJFUV MN15L\/Def2-QZVPP NBO7 LP ( 2) S 6 LV ( 1)Ti 1 30.92\/ LP ( 2) S 2 . LV ( 2)Ti 1 22.06 LP ( 1) O 7 . LV ( 3)Ti 1 55.84\/ LP ( 3) O 7 . LV ( 2)Ti 1 31.53\", 2026. https:\/\/doi.org\/10.5281\/zenodo.22691392<\/a>\n\n<\/li>\n
  5. H.S. Rzepa, and J.D. Woollins, \"Identifying the origins of the ring-size specificity of transition metals for polysulfide anions\", Dalton Transactions<\/i>, 2026. https:\/\/doi.org\/10.1039\/d6dt01849a<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    In the previous post we described the orbital interactions involved in stabilising the formation of a Cp2TiS5 complex (figure 1 below, X=S) rather than a Cp2TiS4 complex when Cp2TiCl2 is treated with a mixture of polysulfide dianions – and how these interactions can be “tuned” by variation in the ring atoms. Figure 1. Bis-cyclopentadienyl titanium […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"federated","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2},"jetpack_post_was_ever_published":false,"_ppma_block_editor_authors":""},"categories":[1745,4],"tags":[],"ppma_author":[2661],"class_list":["post-32008","post","type-post","status-publish","format-standard","hentry","category-crystal_structure_mining","category-interesting-chemistry"],"yoast_head":"\nExploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide. - Henry Rzepa's Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Exploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"In the previous post we described the orbital interactions involved in stabilising the formation of a Cp2TiS5 complex (figure 1 below, X=S) rather than a Cp2TiS4 complex when Cp2TiCl2 is treated with a mixture of polysulfide dianions – and how these interactions can be “tuned” by variation in the ring atoms. Figure 1. Bis-cyclopentadienyl titanium […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2026-09-14T13:51:36+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-09-14T14:04:25+00:00\" \/>\n<meta name=\"author\" content=\"Henry Rzepa\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Henry Rzepa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimated reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"4 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Exploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide. - Henry Rzepa's Blog","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008","og_locale":"en_GB","og_type":"article","og_title":"Exploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide. - Henry Rzepa's Blog","og_description":"In the previous post we described the orbital interactions involved in stabilising the formation of a Cp2TiS5 complex (figure 1 below, X=S) rather than a Cp2TiS4 complex when Cp2TiCl2 is treated with a mixture of polysulfide dianions – and how these interactions can be “tuned” by variation in the ring atoms. Figure 1. Bis-cyclopentadienyl titanium […]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008","og_site_name":"Henry Rzepa's Blog","article_published_time":"2026-09-14T13:51:36+00:00","article_modified_time":"2026-09-14T14:04:25+00:00","author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"4 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"Exploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide.","datePublished":"2026-09-14T13:51:36+00:00","dateModified":"2026-09-14T14:04:25+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008"},"wordCount":603,"commentCount":0,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008#primaryimage"},"thumbnailUrl":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2026\/09\/Cp2TiS5.svg","articleSection":["crystal_structure_mining","Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32008","name":"Exploring the effect that causes ring-size specificity of transition metals for polysulfide dianions: Cyclopentadienyl-2,6-di-isopropylphenoxy Titanium pentasulfide. - 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Thus when the\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":26147,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=26147","url_meta":{"origin":32008,"position":1},"title":"Diberyllocene — and Lithioborocene?","author":"Henry Rzepa","date":"June 18, 2023","format":false,"excerpt":"Sometimes, the properties of a molecule are predicted long before it is synthesised. One such is diberyllocene. I first encountered a related molecule, beryllocene itself, many moons ago. This was unusual because unlike the original metallocenes, the metal atom was not symmetrically disposed between the two cyclopentadienyl faces. Now diberyllocene\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2023\/06\/Screenshot-21-1024x596.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":29121,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29121","url_meta":{"origin":32008,"position":2},"title":"Why an Electron-Withdrawing Group is an o, m-Director rather than m-Director in Electrophilic Aromatic Substitution: The example of CN vs NC.","author":"Henry Rzepa","date":"July 22, 2025","format":false,"excerpt":"In the previous post I followed up on an article published on the theme \"Physical Organic Chemistry: Never Out of Style\". Paul Rablen presented the case that the amount of o (ortho) product in electrophilic substitution of a phenyl ring bearing an EWG (electron withdrawing group) is often large enough\u2026","rel":"","context":"In "reaction mechanism"","block_context":{"text":"reaction mechanism","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1086"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":30548,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30548","url_meta":{"origin":32008,"position":3},"title":"Molecules of the year 2025: Benzene-busting inverted sandwich.","author":"Henry Rzepa","date":"January 1, 2026","format":false,"excerpt":"Sandwich compounds are the colloquial term used for molecules where a metal atom such as an iron dication is \"sandwiched\" between two carbon-based rings as ligands, most commonly cyclopentadienyl anion (the \"bread\") as in e.g. Ferrocene - a molecule first discovered in 1951. An \"inverted\" sandwich is where the carbon\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":28407,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28407","url_meta":{"origin":32008,"position":4},"title":"Cyclo-Heptasulfur, S7 – a classic anomeric effect discovered during a pub lunch!","author":"Henry Rzepa","date":"May 16, 2025","format":false,"excerpt":"Way back in 1977, the crystal structure of the sulfur ring S7 was reported. The authors noted that \"The \u03b4 modification of S7 contains bonds of widely differing length: this has never been observed before in an unsubstituted molecule.\" No explanation was offered, although they note that similar effects have\u2026","rel":"","context":"In "crystal_structure_mining"","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":30890,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30890","url_meta":{"origin":32008,"position":5},"title":"Valence bond representations with +ve charges on adjacent atoms? An odd titanium complex analysed.","author":"Henry Rzepa","date":"March 8, 2026","format":false,"excerpt":"A few posts back, I contemplated the curly arrows appropriate for the formation of nitrosobenzene dimer from nitrosobenzene, and commented on the odd nature of the N=N double bond formed in this process.. Odd, because the valence bond representation of this dimer (1 below) has two formally positive adjacent nitrogen\u2026","rel":"","context":"In "Interesting chemistry"","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]}],"jetpack_likes_enabled":false,"authors":[{"term_id":2661,"user_id":1,"is_guest":0,"slug":"admin","display_name":"Henry Rzepa","avatar_url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","author_category":"1","first_name":"Henry","last_name":"Rzepa","user_url":"https:\/\/orcid.org\/0000-0002-8635-8390","job_title":"","description":"Emeritus Professor of Computational Chemistry at Imperial College London."}],"jetpack_featured_media_url":"","_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32008","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=32008"}],"version-history":[{"count":84,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32008\/revisions"}],"predecessor-version":[{"id":32121,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32008\/revisions\/32121"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=32008"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=32008"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=32008"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=32008"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}