{"id":23686,"date":"2021-05-13T17:08:46","date_gmt":"2021-05-13T16:08:46","guid":{"rendered":"https:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=23686"},"modified":"2021-05-16T10:19:01","modified_gmt":"2021-05-16T09:19:01","slug":"a-reality-based-suggestion-for-a-molecule-with-a-metal-m%e2%a9%b8n-quadruple-bond","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=23686","title":{"rendered":"A reality-based suggestion for a molecule with a metal M\u2a78N quadruple bond."},"content":{"rendered":"
\n

I noted in an earlier post<\/a> the hypothesized example of (CO)3<\/sub>Fe\u2a78C[1]<\/a><\/span> as exhibiting a carbon to iron quadruple bond and which might have precedent in known five-coordinate metal complexes where one of the ligands is a “carbide” or C ligand. I had previously mooted<\/a> that the Fe\u2a78C combination might be replaceable by an isoelectronic Mn\u2a78N pair which could contain a quadruple bond to the nitrogen. An isoelectronic alternative to FeC could also be FeN+<\/sup>. Here I explore the possibility of realistic candidates for such bonded nitrogen.<\/p>\n

So I follow the strategy set in the previous post of conducting a crystal structure search of molecules containing the sub-structure L3<\/sub>-MN or L4<\/sub>-MN. Of the 85 hits for the former (FAIR DOI 10.14469\/hpc\/8196<\/a>), I focus on those where N has only one bonded atom (to the metal M) and the ligand L is non-anionic connecting to the metal via<\/i> e.g.<\/em> carbon or phosphorus. This reduces to 11 hits, which in fact contain something similar to the Arduengo “carbene” ligand L shown below, this being known as a phosphine replacement. Here\u00a0I look at one of these molecules, the internal ion-pair where the positive charge on the\u00a0N is balanced by a four-coordinate negative boron, as in HAQLET.[2]<\/a><\/span> (Data DOI: 10.5517\/ccdc.csd.cc1p0mp0<\/a>).<\/p>\n

\"\"<\/a><\/p>\n

As with (CO)3<\/sub>Fe\u2a78C, L3<\/sub>Fe\u2a78N+<\/sup>\u00a0has a filled 18-electron metal valence shell. A\u00a0\u03c9B97XD\/Def2-SVPD calculation on a simplified model (with aryl groups replaced by H) reveals the following NBO localised orbitals.<\/p>\n\n\n\n\n\n\n\n\n\n
M-N, r = 1.475\u00c5.<\/th>\n<\/tr>\n
NBO 72, Occupied, Non-bonding d-orbital<\/th>\nNBO 71, Occupied, Non-bonding d-orbital<\/th>\n<\/tr>\n
\"\"<\/td>\n\"\"<\/td>\n<\/tr>\n
NBO 67 \u03c0 bond<\/th>\nNBO 66 \u03c0 bond<\/th>\n<\/tr>\n
\"\"<\/td>\n\"\"<\/td>\n<\/tr>\n
NBO 59 \u03c3 bond<\/th>\nNBO 27 \u03c3 bond<\/th>\n<\/tr>\n
\"\"<\/td>\n\"\"<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

There are two \u03c3-bonds and two \u03c0-bonds between the Fe and the N. The molecule is presumably inhibited from reaction such as e.g.<\/i> dimerising, because the iron-bonded nitrogen atom sits in a well created by the mesityl groups, thus sterically preventing any N…N approach close enough and at the appropriate angle to unite the two units. The free energy of dimerisation of the unhindered model used above is -49.7 kcal\/mol. <\/p>\n

\"\"<\/a><\/p>\n

I remind that the NBO method being used to ascertain the nature of the bonding here is a binary method, giving localised NBO orbitals with ~2e occupancies that contain an integer number of bonding orbitals between any pair of atoms. In this case, these can point to either a triple or a quadruple M…N bond for such systems and do not allow for a continuum approach where the weight of each localised bond might not be close to an integer. The purpose here is to flag this system for further analysis rather than as a definitive declaration of its quadruple-bonded nature.<\/p>\n

References<\/h2>\n
  1. A.J. Kalita, S.S. Rohman, C. Kashyap, S.S. Ullah, and A.K. Guha, \"Transition metal carbon quadruple bond: viability through single electron transmutation\", Physical Chemistry Chemical Physics<\/i>, vol. 22, pp. 24178-24180, 2020. https:\/\/doi.org\/10.1039\/d0cp03436c<\/a>\n\n<\/li>\n
  2. L. Bucinsky, M. Breza, W. Lee, A.K. Hickey, D.A. Dickie, I. Nieto, J.A. DeGayner, T.D. Harris, K. Meyer, J. Krzystek, A. Ozarowski, J. Nehrkorn, A. Schnegg, K. Holldack, R.H. Herber, J. Telser, and J.M. Smith, \"Spectroscopic and Computational Studies of Spin States of Iron(IV) Nitrido and Imido Complexes\", Inorganic Chemistry<\/i>, vol. 56, pp. 4751-4768, 2017. https:\/\/doi.org\/10.1021\/acs.inorgchem.7b00512<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    I noted in an earlier post the hypothesized example of (CO)3Fe\u2a78C as exhibiting a carbon to iron quadruple bond and which might have precedent in known five-coordinate metal complexes where one of the ligands is a “carbide” or C ligand. I had previously mooted that the Fe\u2a78C combination might be replaceable by an isoelectronic Mn\u2a78N […]<\/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":"","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},"categories":[1745,4],"tags":[],"ppma_author":[2661],"class_list":["post-23686","post","type-post","status-publish","format-standard","hentry","category-crystal_structure_mining","category-interesting-chemistry"],"yoast_head":"\nA reality-based suggestion for a molecule with a metal M\u2a78N quadruple bond. - 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=23686\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"A reality-based suggestion for a molecule with a metal M\u2a78N quadruple bond. - Henry Rzepa's Blog\" \/>\n<meta property=\"og:description\" content=\"I noted in an earlier post the hypothesized example of (CO)3Fe\u2a78C as exhibiting a carbon to iron quadruple bond and which might have precedent in known five-coordinate metal complexes where one of the ligands is a “carbide” or C ligand. I had previously mooted that the Fe\u2a78C combination might be replaceable by an isoelectronic Mn\u2a78N […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=23686\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa's Blog\" \/>\n<meta property=\"article:published_time\" content=\"2021-05-13T16:08:46+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2021-05-16T09:19:01+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2021\/05\/L3FeN.svg\" \/>\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=\"2 minutes\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"A reality-based suggestion for a molecule with a metal M\u2a78N quadruple bond. - 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=23686","og_locale":"en_GB","og_type":"article","og_title":"A reality-based suggestion for a molecule with a metal M\u2a78N quadruple bond. - Henry Rzepa's Blog","og_description":"I noted in an earlier post the hypothesized example of (CO)3Fe\u2a78C as exhibiting a carbon to iron quadruple bond and which might have precedent in known five-coordinate metal complexes where one of the ligands is a “carbide” or C ligand. 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A decade on, and possibly approaching 100 articles by many authors on the topic,\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\/2020\/11\/NMn_33a-1024x839.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":21846,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=21846","url_meta":{"origin":23686,"position":1},"title":"Comment on “Resolving the Quadruple Bonding Conundrum in C2 Using Insights Derived from Excited State Potential Energy Surfaces”: The 7\u03a3 heptet excited states for related molecules.","author":"Henry Rzepa","date":"January 2, 2020","format":false,"excerpt":"I noted in an earlier blog, a potential (if difficult) experimental test of the properties of the singlet state of dicarbon, C2. Now, just a few days ago, a ChemRxiv article has been published suggesting another (probably much more realistic) test.\u00a0This looks at the so-called 7\u03a3 open shell state 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":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2020\/01\/checkpoint_10062095-300x169.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":23777,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=23777","url_meta":{"origin":23686,"position":2},"title":"A suggestion for a molecule with a M\u2a78C quadruple bond with trigonal metal coordination.","author":"Henry Rzepa","date":"May 13, 2021","format":false,"excerpt":"The proposed identification of molecules with potential metal to carbon quadruple bonds, in which the metal exhibits trigonal bipyramidal coordination rather than the tetrahedral modes which have been proposed in the literature,, leads on to asking whether simple trigonal coordination at the metal can also sustain this theme? The rational\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":21009,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=21009","url_meta":{"origin":23686,"position":3},"title":"Diatomics with eight valence-electrons: formation by radioactive decay.","author":"Henry Rzepa","date":"June 2, 2019","format":false,"excerpt":"This is a follow up to my earlier post about C\u2a78N+, itself inspired by this ChemRxiv pre-print which describes a chemical synthesis of singlet biradicaloid C2 and its proposed\u00a0identification as such by chemical trapping. First row diatomics based on the iso-electronic principle of eight valence electrons include both C\u2a78N+ and\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":20933,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=20933","url_meta":{"origin":23686,"position":4},"title":"Startling bonds: revisiting C\u2a78N+, via the helium bond in N\u2261C-He+.","author":"Henry Rzepa","date":"May 27, 2019","format":false,"excerpt":"Although the small diatomic molecule known as dicarbon or C2 has been known for a long time, its properties and reactivity have really only been determined\u00a0via its very high temperature generation. My interest started in 2010, when I speculatively proposed here that the related isoelectronic species C\u2a78N+ might sustain a\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":10733,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=10733","url_meta":{"origin":23686,"position":5},"title":"Is dicarbon (C2) a molecule of chemical interest?","author":"Henry Rzepa","date":"July 3, 2013","format":false,"excerpt":"C2\u00a0(dicarbon) is certainly interesting from a theoretical point of view. Whether or not it can be described as having a quadruple bond has induced much passionate discussion,,,. Its occurrence in space and in flames is also well-known. But does it have what might be called a conventional chemistry? Other highly\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":"Click for 3D","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/07\/LaOsC1.jpeg?resize=350%2C200","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":"Henry Rzepa is Emeritus Professor of Computational Chemistry at Imperial College London."}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/23686","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=23686"}],"version-history":[{"count":32,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/23686\/revisions"}],"predecessor-version":[{"id":23854,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/23686\/revisions\/23854"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=23686"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=23686"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=23686"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=23686"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}