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6 h 6 calculated explicitly using quantum chemical methods b 0 is set perpendicular to the molecular plane in the left subfigure only vectors in the molecular plane are shown in the right subfigure only vectors 1 a u 52 pm above the molecular plane are shown only vectors with a modulus between 0 01 and 0 1 na t are displayed contrasting the schematic picture which gives in analogy to the laws of classical electrodynamics only diatropic contributions the full quantum mechanical picture also yield paratropic contributions as counter clockwise vortices in this diagram these are located in benzene mainly in the molecular plane inside the c 6 ring relative aromaticity edit numerous attempts have been made to quantify aromaticity with respect to the observed ring current 4 one method is called diamagnetic susceptibility exaltation λ defined as the difference between the measured magnetic susceptibility of a compound and a calculated value based on group additivity tables large negative values are aromatic for example benzene λ 13 4 values close to zero are non aromatic for example borazine λ 1 7 and cyclohexane λ 1 1 large positive values are antiaromatic for example cyclobutadiene λ 18 another measurable quantity is the chemical shift of lithium ions li in complexes of lithium with aromatic structures because lithium tends to bond as a π coordination complex to the face of the aromatic rings thus the lithium atom in cyclopentadienyl lithium cpli has a chemical shift of 8 6 ppm aromatic and its cp 2 li complex a shift of 13 1 both methods suffer from the disadvantage that values depend on ring size selected nics values 5 chemical ppm pyrrole 15 1 thiophene 13 6 furan 12 3 naphthalene 9 9 benzene 9 7 tropylium 7 6 cyclopentadiene 3 2 cyclohexane 2 2 pentalene 18 1 heptalene 22 7 cyclobutadiene 27 6 nucleus independent chemical shift edit the nucleus independent chemical shift nics is a computational method that calculates the absolute magnetic shielding at the center of a ring the values are reported with a reversed sign to make them compatible with the chemical shift conventions of nmr spectroscopy 5 in this method negative nics values indicate aromaticity and positive values indicate antiaromaticity 6 7 there are a variety of methods to calculate nics values however the most robust method for calculating nics values involves scanning the molecule in a nicszz scan in this process the nics value is calculated above the rings and this allows for evaluating the aromatics of each ring which is especially useful for polycyclic compounds 8 harmonic oscillator model of aromaticity edit yet another method called the harmonic oscillator model of aromaticity homa 9 is defined as a normalized sum of squared deviations of bond lengths from the optimal value which is assumed to be realized for a fully aromatic system 10 an aromatic compound has homa value 1 whereas a non aromatic compound has value 0 for all carbon systems the homa value is defined as a 1 v n i n d opt d i 2 displaystyle mathrm a 1 frac v n sum _ i n d_ text opt d_ i 2 where v 257 7 å 2 is the normalization value n is the number of carbon carbon bonds and d are bond lengths d opt 1 388 å is the optimal value and d i are the observed or computed values references edit merino gabriel 2004 the induced magnetic field in cyclic molecules chemistry a european journal 10 17 4367 4371 bibcode 2004cheuj 10 4367m doi 10 1002 chem 200400457 pmid 15352120 gomes j a n f 2001 aromaticity and ring currents chemical reviews 101 5 1349 1384 doi 10 1021 cr990323h pmid 11710225 johansson mp jusélius j sundholm d march 2005 sphere currents of buckminsterfullerene angew chem int ed engl 44 12 1843 6 bibcode 2005acie 44 1843j doi 10 1002 anie 200462348 pmid 15706578 what is aromaticity paul von ragué schleyer and haijun jiao pure appl chem vol 68 no 2 pp 209 218 1996 link 1 2 von ragué schleyer paul 1996 nucleus independent chemical shifts a simple and efficient aromaticity probe journal of the american chemical society 118 26 6317 6318 bibcode 1996jachs 118 6317s doi 10 1021 ja960582d pmid 28872872 chen zhongfang wannere chaitanya s corminboeuf clémence puchta ralph schleyer von ragué paul 2005 nucleus independent chemical shifts nics as an aromaticity criterion chemical reviews 105 10 3842 3888 doi 10 1021 cr030088 pmid 16218569 puchta ralph djordjevic sladjana radenkovic slavko jiao haijun 2022 25 years of nics much more than nothing journal of the serbian chemical society 87 12 1439 1446 doi 10 2298 jsc211203057p stanger amnon 2020 06 08 nics past and present european journal of organic chemistry 2020 21 3120 3127 doi 10 1002 ejoc 201901829 issn 1434 193x kruszewski j 1972 definition of aromaticity basing on the harmonic oscillator model tetrahedron letters 13 36 3839 3842 doi 10 1016 s0040 4039 01 94175 9 how far is the π electron delocalization of the phenanthrene moiety modified in the aza analogues and their n oxides beata t stępień tadeusz m krygowski a michał k cyrański jacek młochowski pierluigi orioli and francesco abbate arkivoc 2003 v t e topics in organic reactions addition reaction elimination reaction polymerization reagents rearrangement reaction redox reaction regioselectivity stereoselectivity stereospecificity substitution reaction a value alpha effect annulene anomeric effect antiaromaticity aromatic ring current aromaticity baird s rule baker nathan effect baldwin s rules bema hapothle beta silicon effect bicycloaromaticity bredt s rule bürgi dunitz angle catalytic resonance theory charge remote fragmentation charge transfer complex clar s rule conformational isomerism conjugated system conrotatory and disrotatory curtin hammett principle dynamic binding chemistry edwards equation effective molarity electromeric effect electron rich electron withdrawing group electronic effect electrophile evelyn effect flippin lodge angle free energy relationship grunwald winstein equation hammett acidity function hammett equation george s hammond hammond s postulate homoaromaticity hückel s rule hyperconjugation inductive effect kinetic isotope effect lfer solvent coefficients data page marcus theory markovnikov s rule möbius aromaticity möbius hückel concept more o ferrall jencks plot negative hyperconjugation neighbouring group participation 2 norbornyl cation nucleophile kennedy j p orton passive binding phosphaethynolate polar effect polyfluorene ring strain σ aromaticity spherical aromaticity spiroaromaticity steric effects superaromaticity swain lupton equation taft equation thorpe ingold effect vinylogy walsh diagram woodward hoffmann rules woodward s rules y aromaticity yukawa tsuno equation zaitsev s rule σ bishomoaromaticity list of organic reactions carbon carbon bond forming reactions acetoacetic ester synthesis acyloin condensation aldol condensation aldol reaction alkane metathesis alkyne metathesis alkyne trimerisation alkynylation allan robinson reaction arndt eistert reaction auwers synthesis aza baylis hillman reaction barbier reaction barton kellogg reaction baylis hillman reaction benary reaction bergman cyclization biginelli reaction bingel reaction blaise ketone synthesis blaise reaction blanc chloromethylation bodroux chichibabin aldehyde synthesis bouveault aldehyde synthesis bucherer bergs reaction buchner ring expansion cadiot chodkiewicz coupling carbonyl allylation carbonyl olefin metathesis castro stephens coupling chan rearrangement chan lam coupling claisen condensation claisen rearrangement claisen schmidt condensation combes quinoline synthesis corey fuchs reaction corey house synthesis coupling reaction cross coupling reaction cross dehydrogenative coupling cross coupling partner dakin west reaction darzens reaction diels alder reaction doebner reaction wulff dötz reaction ene reaction enyne metathesis ethenolysis favorskii reaction ferrier carbocyclization friedel crafts reaction fujimoto belleau reaction fujiwara moritani reaction fukuyama coupling gabriel colman rearrangement gattermann reaction glaser coupling grignard reaction grignard reagent hammick reaction heck reaction henry reaction heterogeneous metal catalyzed cross coupling high dilution principle hiyama coupling homologation reaction horner wadsworth emmons reaction hydrocyanation hydrovinylation hydroxymethylation ivanov reaction johnson corey chaykovsky reaction julia olefination julia kocienski olefination kauffmann olefination knoevenagel condensation knorr pyrrole synthesis kolbe schmitt reaction kowalski ester homologation kulinkovich reaction kumada coupling liebeskind srogl coupling malonic ester synthesis mannich reaction mcmurry reaction meerwein arylation methylenation michael reaction minisci reaction mizoroki heck vs reductive heck nef isocyanide reaction nef synthesis negishi coupling nierenstein reaction nitro mannich reaction nozaki hiyama kishi reaction olefin conversion technology olefin metathesis palladium nhc complex passerini reaction peterson olefination pfitzinger reaction piancatelli rearrangement pinacol coupling reaction prins reaction quelet reaction ramberg bäcklund reaction rauhut currier reaction reformatsky reaction reimer tiemann reaction rieche formylation ring closing metathesis robinson annulation sakurai reaction seyferth gilbert homologation shapiro reaction sonogashira coupling stetter reaction stille reaction stollé synthesis stork enamine alkylation suzuki reaction takai olefination thermal rearrangement of aromatic hydrocarbons thorpe reaction ugi reaction ullmann reaction wagner jauregg reaction weinreb ketone synthesis wittig reaction wurtz reaction wurtz fittig reaction zincke suhl reaction homologation reactions arndt eistert reaction hooker reaction kiliani fischer synthesis kowalski ester homologation methoxymethylenetriphenylphosphorane seyferth gilbert homologation wittig reaction olefination reactions bamford stevens reaction barton kellogg reaction boord olefin synthesis chugaev elimination cope reaction corey winter olefin synthesis dehydrohalogenation elimination reaction grieco elimination hofmann elimination horner wadsworth emmons reaction hydrazone iodination julia olefination julia kocienski olefination kauffmann olefination mcmurry reaction peterson olefination ramberg bäcklund reaction shapiro reaction takai olefination wittig reaction carbon heteroatom bond forming reactions azo coupling bartoli indole synthesis boudouard reaction cadogan sundberg indole synthesis diazonium compound esterification grignard reagent haloform reaction hegedus indole synthesis hurd mori 1 2 3 thiadiazole synthesis kharasch sosnovsky reaction knorr pyrrole synthesis leimgruber batcho indole synthesis mukaiyama hydration nenitzescu indole synthesis oxymercuration reaction reed reaction schotten baumann reaction ullmann condensation williamson ether synthesis yamaguchi esterification degradation reactions barbier wieland degradation bergmann degradation edman degradation emde degradation gallagher hollander degradation hofmann rearrangement hooker reaction isosaccharinic acid marker degradation ruff degradation strecker degradation von braun amide degradation weerman degradation wohl degradation organic redox reactions acyloin condensation adkins peterson reaction akabori amino acid reaction alcohol oxidation algar flynn oyamada reaction amide reduction andrussow process angeli rimini reaction aromatization autoxidation baeyer villiger oxidation barton mccombie deoxygenation bechamp reduction benkeser reaction bergmann degradation birch reduction bohn schmidt reaction bosch reaction bouveault blanc reduction boyland sims oxidation cannizzaro reaction carbonyl reduction clemmensen reduction collins oxidation corey itsuno reduction corey kim oxidation corey winter olefin synthesis criegee oxidation dakin oxidation davis oxidation deoxygenation dess martin oxidation dna oxidation elbs persulfate oxidation emde degradation eschweiler clarke reaction étard reaction fischer tropsch process fleming tamao oxidation fukuyama reduction ganem oxidation glycol cleavage griesbaum coozonolysis grundmann aldehyde synthesis haloform reaction hydrogenation hydrogenolysis hydroxylation jones oxidation kiliani fischer synthesis kolbe electrolysis kornblum oxidation kornblum delamare rearrangement leuckart reaction ley oxidation lindgren oxidation lipid peroxidation lombardo methylenation luche reduction markó lam deoxygenation mcfadyen stevens reaction meerwein ponndorf verley reduction methionine sulfoxide miyaura borylation mozingo reduction noyori asymmetric hydrogenation omega oxidation oppenauer oxidation oxygen rebound mechanism ozonolysis parikh doering oxidation pinnick oxidation prévost reaction reduction of nitro compounds reductive amination riley oxidation rosenmund reduction rubottom oxidation sabatier reaction sarett oxidation selenoxide elimination shapiro reaction sharpless asymmetric dihydroxylation epoxidation of allylic alcohols sharpless epoxidation sharpless oxyamination stahl oxidation staudinger reaction stephen aldehyde synthesis swern oxidation transfer hydrogenation wacker process wharton reaction whiting reaction wohl aue reaction wolff kishner reduction wolffenstein böters reaction zinin reaction rearrangement reactions 1 2 rearrangement 1 2 wittig rearrangement 2 3 sigmatropic rearrangement 2 3 wittig rearrangement achmatowicz reaction alkyne zipper reaction allen millar trippett rearrangement allylic rearrangement alpha ketol rearrangement amadori rearrangement arndt eistert reaction aza cope rearrangement baker venkataraman rearrangement bamberger rearrangement banert cascade beckmann rearrangement benzilic acid rearrangement bergman cyclization bergmann degradation boekelheide reaction brook rearrangement buchner ring expansion carroll rearrangement chan rearrangement claisen rearrangement cope rearrangement corey fuchs reaction cornforth rearrangement criegee rearrangement curtius rearrangement demjanov rearrangement di π methane rearrangement dimroth rearrangement divinylcyclopropane cycloheptadiene rearrangement dowd beckwith ring expansion reaction electrocyclic reaction ene reaction enyne metathesis favorskii reaction favorskii rearrangement ferrier carbocyclization ferrier rearrangement fischer hepp rearrangement fries rearrangement fritsch buttenberg wiechell rearrangement gabriel colman rearrangement group transfer reaction halogen dance rearrangement hayashi rearrangement hofmann rearrangement hofmann martius rearrangement ireland claisen rearrangement jacobsen rearrangement kornblum delamare rearrangement kowalski ester homologation lobry de bruyn van ekenstein transformation lossen rearrangement mcfadyen stevens reaction mclafferty rearrangement meyer schuster rearrangement mislow evans rearrangement mumm rearrangement myers allene synthesis nazarov cyclization reaction neber rearrangement newman kwart rearrangement overman rearrangement oxy cope rearrangement pericyclic reaction piancatelli rearrangement pinacol rear...
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