{"id":29383,"date":"2025-08-11T11:27:20","date_gmt":"2025-08-11T10:27:20","guid":{"rendered":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29383"},"modified":"2025-09-03T11:17:14","modified_gmt":"2025-09-03T10:17:14","slug":"the-mysterious-nn-double-bond-in-nitrosobenzene-dimer","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29383","title":{"rendered":"The mysterious N=N double bond in nitrosobenzene dimer."},"content":{"rendered":"
\n

In an earlier blog, I discussed[1]<\/a><\/span> the curly arrows associated with the known dimerisation of nitrosobenzene, and how the\u00a0N=N double bond (shown in red below) forms in a single concerted process.<\/p>\n

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

One of the properties of this molecule is that the equilibrium between the monomer and dimer can be detected[2]<\/a><\/span>, with significant concentrations of the dimer observed below 10\u00b0C. This dimer can even be crystalised, with around 20 well defined crystal structures known for the dimeric structure in the current version of the\u00a0CSD crystal structure dataset. Nitrosobenzene dimer itself forms a cis<\/i> isomer, but others are known as trans<\/i> (see below).<\/p>\n

\"\"<\/p>\n

This detectable equilibrium means that the formal bond dissociation energy of that N=N bond must be very low – close to zero. This makes it an unusually weak double bond! Let’s explore how unusual by adopting a technique for analysing the energies in the molecule known as Natural Energy Decomposition Analysis or NEDA<\/em>[3]<\/a><\/span> (there are several other well-used methods for this, but I will concentrate on this one in this post at least). To explain what it is, I will paraphrase the NBO7 manual:<\/a><\/p>\n

Natural energy decomposition analysis is an energy partitioning procedure for molecular interactions with contributions from Electrical interaction (EL), charge transfer (CT), and core repulsion (CORE) terms as evaluated for self-consistent field (SCF) wavefunctions.<\/em><\/p>\n

    \n
  1. The electrical term <\/i>EL = ES + POL + SE<\/i> <\/strong>arises from classical electrostatic (ES) and polarization interactions (POL+SE). SE is the linear response self energy (energy penalty) of polarization.<\/em><\/li>\n
  2. The CORE contribution <\/i>CORE = EX + DEF \u2212 SE<\/i> <\/strong>results principally from intermolecular exchange interactions (EX) and deformation (DEF), where the latter is the energy cost to distort a fragment wavefunction in the field of all other fragments of the complex. For DFT-based analysis, EX is replaced by the exchange-correlation interaction (XC). <\/em><\/li>\n
  3. The total interaction energy is then given by\u00a0<\/em><\/li>\n
  4. \u0394E = EL + CT + CORE<\/strong><\/em><\/li>\n<\/ol>\n

    So now for some calculations[4]<\/a><\/span>. To do this, one has to consider an appropriate reference state[5]<\/a><\/span> for the two fragments of the molecule, in this case nitrosobenzene itself. This is expressed via a set of charge,multiplicity<\/em> definitions for the supermolecule and all the fragments. For the nitrosobenzene dimer, two possibilities can be considered<\/p>\n

      \n
    1. 0,1 0,1 0,1 (which defines singlet states for all three species)<\/li>\n
    2. 0,1 0,3 0,-3 (which defines triplet states for the two fragments, with a “spin flip” for the second).<\/li>\n<\/ol>\n

      Firstly \u00a0I will calculate \u0394E\u00a0<\/strong> (Z)-1,2-diphenylethene, which is a classical C=C double bond alkene.<\/p>\n

        \n
      1. For the reference state 0,1 0,3 0,-3\n
        Electrical (ES+POL+SE) :  -8691.975\r\n   Charge Transfer (CT) :   -809.587\r\n       Core (XC+DEF-SE) :   9327.995\r\n                        ------------\r\n  Total Interaction (E) :   -173.567<\/strong> kcal\/mol<\/small><\/tt><\/pre>\n<\/li>\n
      2. For the reference state 0,1 0,1 0,1 (which represents two carbenes)\n
         Electrical (ES+POL+SE) :  -7878.192\r\n   Charge Transfer (CT) :   -918.005\r\n       Core (XC+DEF-SE) :   8473.018\r\n                        ------------\r\n  Total Interaction (E) :   -323.179<\/strong> kcal\/mol<\/small><\/tt><\/pre>\n<\/li>\n<\/ol>\n
        So this classical C=C double bond partitions into two interacting triplet carbenes, with a spin flip to align their interaction. Now for nitrosobenzene.<\/p>\n
          \n
        1. For the reference state 0,1 0,1 0,1 (which represents two nitrosobenzenes each with a lone pair of electrons)\n
          Electrical (ES+POL+SE) : -18230.176\r\n   Charge Transfer (CT) :   -818.925\r\n       Core (XC+DEF-SE) :  19021.537\r\n                        ------------\r\n  Total Interaction (E) :    -27.564<\/strong> kcal\/mol<\/small><\/tt><\/pre>\n<\/li>\n
        2. For the reference state 0,1 0,3 0,-3\n
          Electrical (ES+POL+SE) : -17567.592\r\n   Charge Transfer (CT) :   -677.676\r\n       Core (XC+DEF-SE) :  18197.205\r\n                        ------------\r\n  Total Interaction (E) :    -48.063<\/strong> kcal\/mol<\/small><\/tt><\/pre>\n<\/li>\n<\/ol>\n
          This shows completely different behaviour for the nitrosobenzene dimer and (effectively) the phenyl carbene dimer, with a different reference state for the two species. The electrical and charge transfer terms for the former are much larger than for the latter and this analysis does indeed conform the supposition made at the start that the N=N bond in nitrosobenzene dimer is indeed very unusual and very weak! Perhaps the weakest double bond known? If there are other candidates, I would love to hear about them!<\/p>\n
          Finally, I note that the relatively low NEDA energy for a triplet reference state for the nitrosobenzene dimer also matches with the observation made previously[1]<\/a><\/span> that open shell (biradical) wavefunctions are needed to describe the curly arrows for the process.<\/p>\n
          Energy decomposition analysis is a good tool to have in one’s toolbox for analysing molecular behaviour and no doubt I will use it more in the future! Next, tetra-t<\/em>-butylethene!<\/p>\n
          \n
          This post has DOI: 10.59350\/rzepa.29383<\/a><\/p>\n
          References<\/h2>\n    
          1. H. Rzepa, \"Mechanism of the dimerisation of Nitrosobenzene.\", 2025. https:\/\/doi.org\/10.59350\/rzepa.28849<\/a>\n\n<\/li>\n
          2. K.G. Orrell, V. \u0160ik, and D. Stephenson, \"Study of the monomer\u2010dimer equilibrium of nitrosobenzene using multinuclear one\u2010 and two\u2010dimensional NMR techniques\", Magnetic Resonance in Chemistry<\/i>, vol. 25, pp. 1007-1011, 1987. https:\/\/doi.org\/10.1002\/mrc.1260251118<\/a>\n\n<\/li>\n
          3. E.D. Glendening, and A. Streitwieser, \"Natural energy decomposition analysis: An energy partitioning procedure for molecular interactions with application to weak hydrogen bonding, strong ionic, and moderate donor\u2013acceptor interactions\", The Journal of Chemical Physics<\/i>, vol. 100, pp. 2900-2909, 1994. https:\/\/doi.org\/10.1063\/1.466432<\/a>\n\n<\/li>\n
          4. H. Rzepa, \"The mysterious N=N double bond in nitrosobenzene dimer.\", 2025. https:\/\/doi.org\/10.14469\/hpc\/15455<\/a>\n\n<\/li>\n
          5. C.R. Landis, R.P. Hughes, and F. Weinhold, \"Bonding Analysis of TM(cAAC)<sub>2<\/sub> (TM = Cu, Ag, and Au) and the Importance of Reference State\", Organometallics<\/i>, vol. 34, pp. 3442-3449, 2015. https:\/\/doi.org\/10.1021\/acs.organomet.5b00429<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"
            In an earlier blog, I discussed the curly arrows associated with the known dimerisation of nitrosobenzene, and how the\u00a0N=N double bond (shown in red below) forms in a single concerted process. 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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":[]},{"id":28849,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=28849","url_meta":{"origin":29383,"position":1},"title":"Mechanism of the dimerisation of Nitrosobenzene.","author":"Henry Rzepa","date":"June 14, 2025","format":false,"excerpt":"I am in the process of revising my annual lecture to first year university students on the topic of \"curly arrows\". I like to start my story in 1924, when Robert Robinson published the very first example as an illustration of why nitrosobenzene undergoes electrophilic bromination in the para position\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\/06\/trans.gif?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\/06\/trans.gif?resize=350%2C200&ssl=1 1x, https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2025\/06\/trans.gif?resize=525%2C300&ssl=1 1.5x"},"classes":[]},{"id":29626,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29626","url_meta":{"origin":29383,"position":2},"title":"Hydrogenating the even more mysterious N\u2261N triple bond in a nitric oxide dimer.","author":"Henry Rzepa","date":"August 25, 2025","format":false,"excerpt":"Previously I looked at some of the properties of the mysterious dimer of nitric oxide \u00a01 - not the known weak dimer but a higher energy form with a \"triple\" N\u2261N bond. This valence bond isomer of the weak dimer was some 24 kcal\/mol higher in free energy than 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":29429,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29429","url_meta":{"origin":29383,"position":3},"title":"The even more mysterious N\u2261N triple bond in a nitric oxide dimer.","author":"Henry Rzepa","date":"August 18, 2025","format":false,"excerpt":"Previously, I pondered about the strange N=N double bond in nitrosobenzene dimer as a follow up to commenting on the curly arrow mechanism of the dimerisation. By the same curly arrow method, one can produce the below, showing how the simpler nitric oxide radical could potentially dimerise to a species\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":29410,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29410","url_meta":{"origin":29383,"position":4},"title":"Energy decomposition analysis of hindered alkenes: Tetra t-butylethene and others.","author":"Henry Rzepa","date":"August 13, 2025","format":false,"excerpt":"In the previous post, I introduced the N=N double bond in nitrosobenzene dimer, arguing that even though it was a formal double bond, its bond dissociation energy made it nonetheless a very weak double bond! This was backed up by a technique known as energy decomposition analysis or EDA. Here\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":29665,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29665","url_meta":{"origin":29383,"position":5},"title":"Alternative reactions of the N\u2261N “triple bond” in a nitric oxide dimer: forming the trimer N3O3.","author":"Henry Rzepa","date":"September 3, 2025","format":false,"excerpt":"In the previous post I mooted the possibility that a high energy form of the dimer of nitric oxide 1 might nonetheless be able to be detected using suitable traps (such as hydrogenation or cycloaddition). However, an interesting alternative is that this species could be trapped by nitric oxide itself.\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","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\/29383","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=29383"}],"version-history":[{"count":18,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/29383\/revisions"}],"predecessor-version":[{"id":29693,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/29383\/revisions\/29693"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=29383"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=29383"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=29383"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=29383"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}