Review. Benzene on the basis of the three-electron bond. Theory ofthree-electron bond inthe four works with brief comments (review). 2016.
Volodymyr Bezverkhniy


Using the concept ofthree-electron bond we can represent the actual electron structure ofbenzene and other molecules, explain specificity ofthe aromatic bond and calculate the delocalization energy. The aromatic bond is athree-electron bond inflat cyclic systems with aspecific interaction ofelectrons through the cycle. Inbenzene formed anew type ofchemical bonds an aromatic bond, which has amultiplicity ofmore than 1.5(1.66) http://vixra.org/author/bezverkhniy_volodymyr_dmytrovych





Review. Benzene on the basis of the three-electron bond

Theory ofthree-electron bond inthe four works with brief comments (review). 2016.

Volodymyr Dmytrovych Bezverkhniy



Volodymyr Dmytrovych Bezverkhniy,2017

Vitaliy Volodymyrovich Bezverkhniy, ,2017



ISBN978-5-4483-6946-9

     Ridero


Iexpress my deep gratitude tomy son, Bezverkhniy Vitaliy Volodymyrovich, for participation inthe development ofthe theory (some parts as aco-author), and for his invaluable contribution tothe English translation.



Abstract: Using the concept ofthree-electron bond we can represent the actual electron structure ofbenzene and other molecules, explain specificity ofthe aromatic bond and calculate the delocalization energy. Gives theoretical justification and experimental confirmation ofexistence ofthe three-electron bond.

It was shown, that functional relation y = a+ b/x +c/x


fully describes dependence ofenergy and multiplicity ofchemical bond from bond distance.

Keywords: benzene, three-electron bond, semi-virtual particle, fermion, entangled quantum state, Interfering Universe.




1.Introduction


Chemical bond has been always abasis ofchemistry. Advancement ofchemical science can be considered as evolution, development ofconcepts about chemical bond. Aromatic bond is fundamental basis oforganic chemistry. Concept ofthree-electron bond inbenzene molecule enable toexplain specificity ofaromatic bond. It also becomes apparent, why planar molecules with 6, 10etc. electrons (according toH?ckel rule 4n +2) must be aromatic, and planar molecules with 4, 8etc. electrons cannot be aromatic bydefinition.

Description ofchemical bond, that is given byquantum theory, especially interms ofmethod ofmolecular orbitals, is just amathematical model. This model is an approximate representation ofmolecules and its bonds, whereas quantum-mechanical calculations oforganic molecules require considerable simplifications and are extremely complicated.

Concept ofthree-electron bond and developed mathematical relations inthis work are rather simple, illustrative and give exact results ofdifferent values (bond multiplicity, chemical bound energy, delocalization energy ofbenzene). One must clearly imagine, that three-electron bond is joint interaction ofthree electrons with relative spins, that resultsinnew type ofchemical bond (A   A(+ +), A   B (+ +)). This bond type, three-electron bond, makes possible todescribe real molecules oforganic and inorganic compounds without invoking virtual structures, which do not exist inreal terms.

Using ofthree-electron bond before description ofbenzene molecule enables todetermine delocalization energy ofbenzene inan elementary way, understand why multiplicity of- bond ofbenzene is more than 1.5and tounderstand the main point ofaromatic bond ingeneral, which is appeared tobe rather illustrative. Besides, for determination ofdelocalization energy it is not required toselect reference structures. Delocalization energy follows from the concept ofaromaticity ofbenzene and its structure on the basis ofthree-electron bond.

Inote that the three-electron bond todescribe the benzene molecule used W.O.Kermak, R. Robinson and J. J.Thomson at the beginning ofthe 20th century [5,6].






Benzene molecule with three-electron bond (W.O.Kermak and R. Robinson, J. J.Thomson).



But since it is not taken into account the spin ofelectrons, have already started cyclooctatetraene problems and therefore the description ofthe benzene molecule byathree-electron proved unsuccessful. Using the three-electron bond with multiplicity of1.5and take account ofthe spin ofeach electron leads tovery good results inthe description ofthe benzene molecule and explain the aromaticity ingeneral. With the help ofthree-electron bond with multiplicity of1.5can be represented byareal formula ofmany organic and inorganic molecules without the aid ofvirtual structures.




2.Structure ofthe benzene molecule on the basis ofthe three-electronbond





2.1. Results and discussion


Supposing that the chemical bond between two atoms can be established bymeans ofthree electrons with oppositely oriented spins (???) the structure ofthe benzene molecule can be expressed as follows (see figure 1and figure2):






benzene molecule on the basis ofthe three-electronbond,spin



It is interesting topoint out that spins ofcentral electrons on opposite sides have an opposite orientation (see figure 2). Now letus consider indetail the interaction ofsix central electrons between themselves. They will be itemized as shown infigure 2. As the spin ofelectron 1and those ofelectrons 2and 6are oppositely oriented (see figure 2) (1(+), 2(-), 6(-)), electron 1will be attracted toelectrons 2and 6respectively. Lets indicate that the distance between electrons 1and 6or 1and 2is equal to1.210? which can be easily shown taking into account the distance between atoms ofcarbon inbenzene tobe 1.397? and the angle between carbon atoms amount to120degrees. Letus compare the distance between electrons 1and 6and 1and 2bond lengths inethane, ethylene and acetylene[7]:






bond lengths inethane, ethylene, acetylene and distance between electrons (1and 2) inbenzene



As we observe, the distance between central electrons 1and 2and 1and 6ofthebenzene molecule is approximately equal tothat between carbon atoms inthe acetylene molecule, therefore, the interaction between electrons 1(+) and 2(-) and 1(+) and 6(-) has tobe rather considerable. Letus express the attraction with arrows. According tosumming up vectors the resultant vector will be directed tothe centre, which means that electron 1under the influence ofelectrons 2and 6will move tothe centre (figure3):






benzene on the basis ofthe three-electron bond, summing up vectors



If we take alook at electron 4we see the similar situation with it (figure 4) and itwillalso move tothe centre and, more importantly, its spin and that ofelectron 1will be oppositely oriented, i.e. electron 1(+) and electron 4(-) will be attracted through the cycle. Electrons 6(-) and 3(+) and electrons 2(-) and 5(+) will interact similarly. The distance between electrons 1and 4inbenzene is equal to2.420?. It is interesting, that this distance is twice as much than distance between electrons 1and 2, or between electrons 1and 6(1.210? ? 2= 2.420?). This interaction through the cycle constitutes the essence ofthe delocalization ofelectrons, ofcourse together with athree-electron bond. Since besides the three-electron bond inthe benzene molecule there is an interaction through the cycle, meaning that the benzene nucleus undergoes akind ofcompression it is clear that the c-c bond multiplicity inbenzene will exceed1.5.

So, the aromatic system is acyclic system with three-electron bonds where an interaction ofcentral electrons through the cycle is observed. Inthe benzene molecule there are three interactions through the cycle-pairwise between electrons 1(+) and 4(-), 2(-) and 5(+), 3(+) and 6(-), as shown infigure5:






benzene on the basis ofthe three-electron bond, interaction through the cycle



Carbon atoms inbenzene are sp?-hybridized. The three-electron bond between carbon atoms inthe benzene molecule can be represented as follows:








Carbon atoms inbenzene have an octet equal to8(3+3+2= 8). It should be pointedout that due tothe largest distance from the atoms nuclei the central electrons ofthe three-electron bond are supposed tobe the most mobile compared toother electrons ofthe three-electron bond. The interaction ofcentral electrons with opposite spins through the cycle can easily explain why cyclobutadiene and cyclooctatetraene are not aromatic compounds:






cyclobutadiene and cyclooctatetraene (three-electron bond)



As we see both incyclobutadiene and cyclooctatetraene, electrons interacting through the cycle have the same spins and, clearly, will be repulsed, therefore there will be no interaction through the cycle and the molecule will not be aromatic. Incyclobutadiene at the expense ofsmall distance it causes the appearance ofantiaromatic properties, and incyclooctatetraene there is apossibility offormation ofnon-planar molecule, where interaction ofcentral electrons becomes impossible and molecule losing the interaction through the cycle loses also three-electron bonds, that results inastructure, inwhich single and double bonds alternate.

Explanation, that cyclooctatetraene is non-aromatic, because it is non-planar and does not hold water, insomuch as dianion ofcyclooctatetraene is aromatic and has planar structure [8],[9].






Planar



X-ray crystal structure analysis determined crystal structure ofpotassium salt ofdianion 1,3,5,7-tetramethylcyclooctatetraene [10], [11].

Octatomic cycle is planar with lengths of- bonds nearly 1.41?.






Planar



From the mentioned above we can make aconclusion: cyclooctatetraene conforms tothe shape ofbath tub not because ofhigh angular pressure (15) at planar structure, but because byinteraction through the cycle central electrons ofthree-electron bonds have equal spin and will push away. Thus for energy reduction cyclooctatetraene conforms tothe shape ofbath tub and becomes non-planar, that disables interaction ofcentral electrons.

Cyclobutadiene represents rectangular high reactivity diene [8, p.79].

It is also interesting toobserve cyclodecapentaene (cis-isomer [10] -annulene).






cyclodecapentaene (three-electron bond)






cyclodecapentaene, distance



Whereas central electrons ofthree-electron bonds have opposite spins, then interaction through the cycle is possible. But distances between central electrons on opposite sides, which interact through the cycle, are extremely long (4.309? if accept L- = 1.400? for regular decagon), angular pressure is high (24) and thats why stabilization at the expense ofinteraction through the cycle at such long distance will be low and cannot cover energy consumption for creation ofplanar molecule.




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