{"id":28515,"date":"2025-05-19T07:17:45","date_gmt":"2025-05-19T06:17:45","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28515"},"modified":"2025-05-29T11:59:40","modified_gmt":"2025-05-29T10:59:40","slug":"cycloheptasulfur-sulfoxide-s7o-anomeric-effects-galore","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28515","title":{"rendered":"Cycloheptasulfur sulfoxide, S7<\/sub>O – Anomeric effects galore!"},"content":{"rendered":"
\n

The monosulfoxide of cyclo-heptasulfur was reported along with cycloheptasulfur itself in 1977,[1]<\/a><\/span> along with the remarks that “The \u03b4 modification of S7<\/sub> contains bonds of widely differing length: this has never been observed before in an unsubstituted molecule.<\/em> and “the same effect having also been observed in other sulfur rings (S8<\/sub>O, S7<\/sub>I1+<\/sup> and S7<\/sub>O).” Here I take a look at the last of these other molecules, the monosulfoxide of S7<\/sub>, as a follow up to the commentary on S7<\/sub> itself.[2]<\/a><\/span> <\/p>\n

The axial oxygen isomer is calculated as being 3.68 kcal\/mol more stable than the equatorial form[3]<\/a><\/span> and a comparison of its calculated (MN15L\/Def2-TZVPP) and observed structure is shown below. The S-S lengths do indeed vary widely.<\/p>\n

\"\"<\/p>\n

As before, an explanation is provided by analysing the orbitals of the molecule using NBO7<\/a>. The interactions tabled below are ordered by the largest first. That from the oxygen into the S4-S5 antibonding NBO (28.2 kcal\/mol) is the biggest I have observed for an anomeric effect involving an S-S bond. The greatest all-sulfur effect (16.8 kcal\/mol) is increased compared to that previously found for S7<\/sub> itself (12.35 kcal\/mol). <\/p>\n\n\n\n\n\n\n\n\n\n\n
Donor lone Pair<\/td>\nAcceptor antibonding NBO<\/td>\nE(2), kcal\/mol<\/td>\nAcceptor bond distance, Å<\/td>\n<\/tr>\n
O8<\/td>\nS4-S5<\/td>\n28.2<\/td>\n2.28<\/td>\n<\/tr>\n
O8<\/td>\nS5-S6<\/td>\n20.2<\/td>\n2.15<\/td>\n<\/tr>\n
S7<\/td>\nS4-S5<\/td>\n16.8<\/td>\n2.28<\/td>\n<\/tr>\n
S4<\/td>\nS3-S7<\/td>\n14.8<\/td>\n2.18<\/td>\n<\/tr>\n
S2<\/td>\nS3-S7<\/td>\n12.5<\/td>\n2.18<\/td>\n<\/tr>\n
S3<\/td>\nS5-S6<\/td>\n10.3<\/td>\n2.15<\/td>\n<\/tr>\n
O8<\/td>\nS5-S6<\/td>\n9.6<\/td>\n2.15<\/td>\n<\/tr>\n
S6<\/td>\nS1-S2<\/td>\n9.1<\/td>\n2.10<\/td>\n<\/tr>\n<\/table>\n
\n\n\n\n\n\n\n\n\n\n\n
E(2)<\/td>\nNBO overlaps‡<\/sup> Click on image to load 3D rotatable model<\/td>\n<\/tr>\n
28.2<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

20.0<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

16.8<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

14.8<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

12.5<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

10.3<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

9.6<\/td>\n\n

\"\" <\/td>\n<\/tr>\n

9.1<\/td>\n\n

\"\" <\/td>\n<\/tr>\n<\/table>\n

The S-S stretching modes also vary by more than a factor of two; ν4-7<\/sub> 619 cm-1<\/sup>, ν2-3<\/sub> 528 cm-1<\/sup>, ν1-6<\/sub> 548 cm-1<\/sup>, ν3-7<\/sub> 368 cm-1<\/sup>, ν5-6<\/sub> 331 cm-1<\/sup>, ν4-5<\/sub> 287 cm-1<\/sup>.
\n\"\"
\nIt is indeed remarkable that this small molecule can exhibit as many as eight different anomeric interactions, including two unusually large ones and three regular ones. The result is the profusion of different S-S bond lengths originally commented[1]<\/a><\/span> on accompanied by the wide variety of S-S stretching modes. Can this record be beaten, either in the number or the magnitude of the effects. The answer is YES, but not for a known molecule. See next post! <\/p>\n

References<\/h2>\n
  1. R. Steudel, R. Reinhardt, and T. Sandow, \"Bond Interaction in Sulfur Rings: Crystal and Molecular Structure of <i>cyclo<\/i>\u2010Heptasulfur Oxide, S<sub>7<\/sub>O\", Angewandte Chemie International Edition in English<\/i>, vol. 16, pp. 716-716, 1977. https:\/\/doi.org\/10.1002\/anie.197707161<\/a>\n\n<\/li>\n
  2. H. Rzepa, \"Cyclo-Heptasulfur, S<sub>7<\/sub> \u2013 a classic anomeric effect discovered during a pub lunch!\", 2025. https:\/\/doi.org\/10.59350\/rzepa.28407<\/a>\n\n<\/li>\n
  3. H. Rzepa, \"Cyclo-Heptasulfur, S7 \u2013 a classic anomeric effect discovered during a pub lunch!\", 2025. https:\/\/doi.org\/10.14469\/hpc\/15228<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    The monosulfoxide of cyclo-heptasulfur was reported along with cycloheptasulfur itself in 1977, along with the remarks that “The \u03b4 modification of S7 contains bonds of widely differing length: this has never been observed before in an unsubstituted molecule. and “the same effect having also been observed in other sulfur rings (S8O, S7I1+ and S7O).” Here […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"","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}},"categories":[4,1086],"tags":[],"ppma_author":[2661],"class_list":["post-28515","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","category-reaction-mechanism-2"],"yoast_head":"\nCycloheptasulfur sulfoxide, S7O - Anomeric effects galore! - 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=28515\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Cycloheptasulfur sulfoxide, S7O - Anomeric effects galore! - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"The monosulfoxide of cyclo-heptasulfur was reported along with cycloheptasulfur itself in 1977, along with the remarks that “The \u03b4 modification of S7 contains bonds of widely differing length: this has never been observed before in an unsubstituted molecule. and “the same effect having also been observed in other sulfur rings (S8O, S7I1+ and S7O).” Here […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28515\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2025-05-19T06:17:45+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-05-29T10:59:40+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":"Cycloheptasulfur sulfoxide, S7O - Anomeric effects galore! 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Here is the largest so far, for the compound S7I1+ The calculated geometry is shown below, with the crystallographic values in parentheses - the two matching very well. 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":28407,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28407","url_meta":{"origin":28515,"position":1},"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":28615,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28615","url_meta":{"origin":28515,"position":2},"title":"5-Imino-5\u03bb4-heptathiepane 3-oxide. More exuberent anomeric effects.","author":"Henry Rzepa","date":"May 20, 2025","format":false,"excerpt":"The two previous \u00a0posts, on the topic of anomeric effects in 7-membered sulfur rings illustrated how orbital interactions between the lone pairs in the molecules and S-S bonds produced widely varying S-S bond lengths in the molecules, some are shorter than normal (which is ~2.05\u00c5 for e.g. the S8 ring)\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":29711,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29711","url_meta":{"origin":28515,"position":3},"title":"Mechanism of reaction between titanocene pentasulfide and sulfenyl chloride: The effect of continuum solvation on the energy surface.","author":"Henry Rzepa","date":"December 16, 2025","format":false,"excerpt":"An investigation of the kinetics of the reaction between titanocene pentasulfide and sulfenyl chloride leading to the formation of the S7 allotrope of sulfur was accompanied by supporting DFT calculations which led to the conclusion\u00a0that of five possible\u00a0mechanisms for the reaction, the most probable corresponded to a variant of the\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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2025\/11\/BL12-17.jpg?resize=350%2C200&ssl=1","width":350,"height":200,"srcset":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2025\/11\/BL12-17.jpg?resize=350%2C200&ssl=1 1x, https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2025\/11\/BL12-17.jpg?resize=525%2C300&ssl=1 1.5x, https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2025\/11\/BL12-17.jpg?resize=700%2C400&ssl=1 2x"},"classes":[]},{"id":29892,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29892","url_meta":{"origin":28515,"position":4},"title":"Reinvestigating the reported transition state structure of a concerted triple H-tunneling mechanism.","author":"Henry Rzepa","date":"November 21, 2025","format":false,"excerpt":"Substituting a deuterium isotope (2H) for a normal protium hydrogen isotope can slow the rate of a chemical reaction if this atom is involved in the reaction mode. The magnitude of the effect,\u00a0referred to as a kinetic isotope effect or KIE is normally 2-7, but higher values of 20 or\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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2025\/11\/FOTBAR.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":15415,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=15415","url_meta":{"origin":28515,"position":5},"title":"I\u2019ve started so I\u2019ll finish. The ionisation mechanism and kinetic isotope effects for 1,3-dimethylindolin-2 one","author":"Henry Rzepa","date":"January 7, 2016","format":false,"excerpt":"This is the third and final study deriving from my Ph.D.. The first two topics dealt with the mechanism of heteroaromatic electrophilic attack using either a diazonium cation or a proton as electrophile, followed by either proton abstraction or carbon dioxide loss from the resulting Wheland intermediate. This final study\u2026","rel":"","context":"In "Historical"","block_context":{"text":"Historical","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=565"},"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","0":null,"1":"","2":"","3":"","4":"","5":"","6":"","7":"","8":""}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/28515","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=28515"}],"version-history":[{"count":87,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/28515\/revisions"}],"predecessor-version":[{"id":28751,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/28515\/revisions\/28751"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=28515"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=28515"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=28515"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=28515"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}