{"id":32368,"date":"2026-10-04T07:38:19","date_gmt":"2026-10-04T06:38:19","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32368"},"modified":"2026-10-04T07:42:13","modified_gmt":"2026-10-04T06:42:13","slug":"molecular-structure-representation-of-sulfur-nitride-systems-are-lewis-structures-useful-here","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32368","title":{"rendered":"Molecular structure representation of sulfur-nitride systems: Are Lewis structures useful here?"},"content":{"rendered":"
\n

I posed[1]<\/a><\/span> this question back in 2010: “(Almost) 100 years of Lewis[2]<\/a><\/span> structures: are they still fit for purpose?”. I was reminded of this when I came across this relatively recent article[3]<\/a><\/span> describing the structures of three binary sulfur-nitrogen anions, as shown in Figure 1 of their article. These are reproduced below (Scheme 1) along with an additional S\/N molecule reported separately.[4]<\/a><\/span>
\n\"\"<\/a> Scheme 1<\/strong>. Molecular structure representations of sulfur nitrides.<\/p>\n

Lewis structures are of course widely exploited in organic chemistry, but apparently less so in inorganic chemistry. Not only are there simple heuristic rules for deriving them, these can be checked using pretty rigorous quantum mechanical procedures, using a method known as NBO7.[5]<\/a><\/span> Thus the NBO7 derived Lewis structures are placed below the literature representations in scheme 1.[6]<\/a><\/span>,[7]<\/a><\/span>,[8]<\/a><\/span>,[9]<\/a><\/span> Each of the structures has interesting features which a Lewis structure can help tease out.<\/p>\n

S4<\/sub>N–<\/sup><\/h4>\n

The S=N=S representational motif is often used in sulfur-nitrogen chemistry, but in organic molecules four-valent nitrogen occurs only as a positively charged cation, and equally sulfur atoms with three substituents (or one double and one single bond) are represented as positively charged cations, whilst sulfur atoms with just one bond are always negatively charged sulfur anions. So none of the four atoms in this literature structure correspond to a Lewis-style representation. The NBO7-derived diagram fully conforms to the “organic” rules, and now contains three charged S atoms.<\/p>\n

S3<\/sub>N3<\/sub>–<\/sup><\/h4>\n

This is of interest since it is regarded as an “aromatic molecule” conforming to the 4n+2 rule for aromaticity. But the literature diagram implies n=1 (six cyclically conjugated \u03c0-electrons). In fact for the NBO7 derived representation, n=2 making ten \u03c0-electrons or a difference of four electrons! I should mention here that NBO7 orbitals are not “symmetry adapted”, ie<\/em> they need not reflect molecular symmetry – this being another difference between the literature and the NBO7 representations.<\/p>\n

S4<\/sub>N5<\/sub>–<\/sup><\/h4>\n

The literature representation contains one negatively charged atom, the tetravalent nitrogen. In fact such a structure is highly improbable, since the valence shell of the nitrogen would have to exceed 8 electrons. Two of the S atoms are depicted as trivalent neutral and three nitrogens are divalent neutral – all non-conformant with organic Lewis structures. With the NBO7 representation, all the atoms are charged, four +ve S and five -ve N. But there is a far more significant difference, the NBO7 version has an additional S-S bond (red in scheme).\u00a0Without this, any attempt at Lewis representation must result in four +ve S and three -ve N and hence the wrong overall charge on the system (S4<\/sub>N5<\/sub>+<\/sup>).<\/p>\n

Conclusions<\/h3>\n

Lewis representations for the four sulfur nitrides shown here are easily validated using NBO7 calculations. In the example of S<\/sub>3<\/sub>N3<\/sub>–<\/sup>, this representation is useful in helping to correctly identify the number of \u03c0-electrons to be used in any aromaticity rule. With S4<\/sub>N5<\/sub>–<\/sup> the Lewis representation requires a two-electron S-S bond to be present (hence the difference of two electrons between S4<\/sub>N5<\/sub>+<\/sup> and S4<\/sub>N5<\/sub>–<\/sup>) and the neutral S5<\/sub>N6<\/sub> has a similar S-S bond.<\/p>\n

References<\/h2>\n
  1. H. Rzepa, \"(Almost) 100 years of Lewis structures: are they still fit for purpose?\", 2010. https:\/\/doi.org\/10.59350\/rncje-xe063<\/a>\n\n<\/li>\n
  2. G.N. Lewis, \"THE ATOM AND THE MOLECULE.\", Journal of the American Chemical Society<\/i>, vol. 38, pp. 762-785, 1916. https:\/\/doi.org\/10.1021\/ja02261a002<\/a>\n\n<\/li>\n
  3. R. Boer\u00e9, T. Roemmele, and M. Krall, \"A Variable Temperature X-ray Diffraction Investigation of [PPN+][S4N5\u2212]: Supramolecular Interactions Governing an Order\/Disorder Transformation and the First High Resolution X-ray Structure of the Anion\", Molecules<\/i>, vol. 19, pp. 1956-1975, 2014. https:\/\/doi.org\/10.3390\/molecules19021956<\/a>\n\n<\/li>\n
  4. T. Chivers, and J. Proctor, \"Preparation and crystal structure of a new sulphur nitride, S5N6; a molecular basket\", Journal of the Chemical Society, Chemical Communications<\/i>, pp. 642, 1978. https:\/\/doi.org\/10.1039\/c39780000642<\/a>\n\n<\/li>\n
  5. E.D. Glendening, C.R. Landis, and F. Weinhold, \"<i>NBO 7.0<\/i>\n : New vistas in localized and delocalized chemical bonding theory\", Journal of Computational Chemistry<\/i>, vol. 40, pp. 2234-2241, 2019. https:\/\/doi.org\/10.1002\/jcc.25873<\/a>\n\n<\/li>\n
  6. H. Rzepa, \"SSNSS\", 2026. https:\/\/doi.org\/10.5281\/zenodo.23118031<\/a>\n\n<\/li>\n
  7. H. Rzepa, \"S3N3 (-) NBO7\", 2026. https:\/\/doi.org\/10.5281\/zenodo.23086044<\/a>\n\n<\/li>\n
  8. H. Rzepa, \"Tetrasulfur pentanitride anion, MN15L\/Def2-TZVPP NBO7\", 2026. https:\/\/doi.org\/10.5281\/zenodo.23120288<\/a>\n\n<\/li>\n
  9. H. Rzepa, \"S5N6 MN15L\/Def2-TZVPP, C2 symmetry NBO7\", 2026. https:\/\/doi.org\/10.5281\/zenodo.23118480<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    I posed this question back in 2010: “(Almost) 100 years of Lewis structures: are they still fit for purpose?”. I was reminded of this when I came across this relatively recent article describing the structures of three binary sulfur-nitrogen anions, as shown in Figure 1 of their article. These are reproduced below (Scheme 1) along […]<\/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":[1,7],"tags":[],"ppma_author":[2661],"class_list":["post-32368","post","type-post","status-publish","format-standard","hentry","category-general","category-hypervalency"],"yoast_head":"\nMolecular structure representation of sulfur-nitride systems: Are Lewis structures useful here? - 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=32368\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Molecular structure representation of sulfur-nitride systems: Are Lewis structures useful here? - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"I posed this question back in 2010: “(Almost) 100 years of Lewis structures: are they still fit for purpose?”. I was reminded of this when I came across this relatively recent article describing the structures of three binary sulfur-nitrogen anions, as shown in Figure 1 of their article. 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I was reminded of this when I came across this relatively recent article describing the structures of three binary sulfur-nitrogen anions, as shown in Figure 1 of their article. 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Quite a trio of Nobel-prize winning molecular structural analyses, all based on a large dose of intuition. The structures of both proteins and DNA succumbed\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.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2011\/04\/ferrocene-aim.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":2559,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=2559","url_meta":{"origin":32368,"position":1},"title":"(Almost) 100 years of Lewis structures: are they still fit for purpose?","author":"Henry Rzepa","date":"September 27, 2010","format":false,"excerpt":"The molecule below was characterised in 1996 and given the name tris(dithiolene)vanadium (IV). No attempt was made in the original article to give this molecule a Lewis structure using Lewis electron pair bonds. This blog will explore some of the issues that arise when this is attempted.1 The name given\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\/2010\/09\/V1.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":31892,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=31892","url_meta":{"origin":32368,"position":2},"title":"Identifying the origins of the ring-size specificity of transition metals for polysulfide anions: “tuning” the effect.","author":"Henry Rzepa","date":"September 10, 2026","format":false,"excerpt":"A recently published article addresses the long standing problem of why transition metals complexes such as e.g. Cp2TiCl2 in the presence of solutions of polysulfide dianions containing sulfur chains of various lengths, can react to form sulfur ring complexes of a specific size, depending on the metal. 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":32123,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=32123","url_meta":{"origin":32368,"position":3},"title":"Unrecognised inorganic metalla-aromatic rings? The mystery of (cyclo-N,S)-titanocenes.","author":"Henry Rzepa","date":"October 3, 2026","format":false,"excerpt":"Metalla-aromatics have been defined as metallacycles that are derived from the formal replacement of a carbon atom in the framework of an organic aromatic ring with a metal fragment.. Here I explore whether this simple definition can be broadened to sulfur-nitrogen rings which contain few, if indeed any,,, carbon atoms\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":28773,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28773","url_meta":{"origin":32368,"position":4},"title":"Cyclo-S6 (Hexathiane) – anomeric effects again!","author":"Henry Rzepa","date":"June 1, 2025","format":false,"excerpt":"I thought I was done with exploring anomeric effects in small sulfur rings. However, I then realised that all the systems\u00a0that I had described had an odd number of atoms and that I had not looked at any even numbered rings. Thus hexasulfur is a smaller (known) ring version of\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":22865,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=22865","url_meta":{"origin":32368,"position":5},"title":"Room-temperature superconductivity in a carbonaceous sulfur hydride!","author":"Henry Rzepa","date":"October 17, 2020","format":false,"excerpt":"The title of this post indicates the exciting prospect that a method of producing a room temperature superconductor has finally been achived. This is only possible at enormous pressures however; >267 gigaPascals (GPa) or 2,635,023 atmospheres. The system is made by milling a mixture of elemental carbon and sulfur, followed\u2026","rel":"","context":"In "Chemical IT"","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2020\/10\/41586_2020_2801_Fig9_ESM-1024x434.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"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\/32368","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=32368"}],"version-history":[{"count":41,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32368\/revisions"}],"predecessor-version":[{"id":32430,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/32368\/revisions\/32430"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=32368"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=32368"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=32368"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=32368"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}

S5<\/sub>N6<\/sub><\/h4>\n

This neutral molecule was reported[4]<\/a><\/span> without any attempt at a Lewis representation, which is shown here with five +ve S and five -ve N atoms and again having an S-S bond (Figure 1) with the same motif as for S4<\/sub>N5<\/sub>–<\/sup>.<\/p>\n

\"\"
\nFigure 1<\/strong>. The S-S bond in S5<\/sub>N6 (red).<\/p>\n