IUPAC Gold Book - Sum formula index

Sum formulas

Without exact chemical meaning

^.⁺	radical ion
^.⁻	radical ion
A	atom–molecule complex mechanism
A	Brønsted relation
A	catalytic hydrogenolysis
A	dimerization
A	electron-transfer catalysis
A	heterolytic dissociative adsorption
A	homolytic dissociative adsorption
A	isotopic fractionation factor
A	kinetic isotope effect
A	light-atom anomaly
A	potential-energy (reaction) surface
A	repulsive potential-energy surface
A⁻	Brønsted relation
A⁻	heteroconjugation
A⁻	homoconjugation
A^.	heterolytic bond-dissociation energy
A'H	heteroconjugation
A⁺	heterolytic bond-dissociation energy
A⁺^.	electron-transfer catalysis
A_1-xB_x	chemical diffusion
A₂	atom–molecule complex mechanism
A₂	dimerization
A–B	heterolytic bond-dissociation energy
A–B	light-atom anomaly
A–B	potential-energy (reaction) surface
A–B	repulsive potential-energy surface
abC=C=Ccd	chirality axis
abC=Cc₂	pro-E, pro-Z
AcO⁻	ligands
AH	homoconjugation
AM	atom–molecule complex mechanism
ArCR₂–	benzylic groups
ArNRNRAr	hydrazo compounds
As_nH_n+2	arsanes
AsR₃	arsenides
B	catalytic hydrogenolysis
B	conjugate acid–base pair
B	electron-transfer catalysis
B	heterolytic dissociative adsorption
B	homoconjugation
B	homolytic dissociative adsorption
B	ionic conductivity
B	isotopic fractionation factor
B	light-atom anomaly
B⁻	heterolytic bond-dissociation energy
B^.	heterolytic bond-dissociation energy
B'	heteroconjugation
B⁺^.	electron-transfer catalysis
BC	light-atom anomaly
BH⁺	conjugate acid–base pair
Bi_nH_n+2	bismuthanes
BuLi	organometallic compounds
C	light-atom anomaly
c	pro-R, pro-S
C(OR')₄	ortho esters
C=X	bisecting conformation (eclipsing conformation)
C₂H₄DBr⁺^.	isotopic molecular ion
C_5n	terpenes
C₆H₅Z	partial rate factor
Cabcd	chirality centre
CaCl₂·nROH	alcoholates
C–D	steric isotope effect
CDCl₃	chemical shift, $δ$ in NMR
Ce	symmetry-conserving transition
[(CH)_a(BH)_mH_b]^c	carbaboranes
(CH)_n	polyhedranes
–[CH₂]_n–	cyclophanes
CH₂D⁺	isotopic ion
CH₂D₂	isotopologue
CH₂D₂	principal ion in mass spectrometry
CH₂DCH=O	isotopomer
CH₂DCO₂H	prochirality
CH₃(CH₂)_nCO₂⁻M⁺	amphiphilic
CH₃(CH₂)_nN⁺(CH₃)₃X⁻	amphiphilic
CH₃(CH₂)_nSO₃⁻M⁺	amphiphilic
CH₃CD=O	isotopomer
CH₃CH=CHD	isotopomer
CH₃CHDOH	isotopomer
CH₃CHDOH	prochirality
CH₃CHOHCHDCH₃	prochirality
CH₃D	isotopologue
CHDTCO₂H	prochirality
CHX₃	haloforms
Cl₃C[CH₂CHPh]_nBr	telomerization
C_n(H₂O)_n	carbohydrates
C_nH_2n	alkenes
–C_nH_2n+1	alkyl groups
C_nH_2n+2	alkanes
C_nH_2n-2	alkynes
C_nH_n	annulenes
C_nH_n+1	annulenes
C–R	bisecting conformation (eclipsing conformation)
–CR₂–CH₂–CR₂–	meso structures in polymers
–CR₂–CR₂O–	crown
–CR₂H	isonitroso compounds
D	organically modified silica
D₂O	chemical shift, $δ$ in NMR
D₂O	gaseous diffusion separator in atmospheric chemistry
D₂O	heavy water
D₂O	pH
DF	branching ratio
DF	chemical laser
DF	molecular laser
ΔE	isostructural reaction
Er³⁺	solid state lasers
[Fe(2-pic)₃]Cl₂·EtOH	spin crossover
GdFeO₃	magnetic transition
GY	cross-conjugation
H(CH₂)_n	alkyl groups
H[CH(OH)]_nC(=O)H	aldoses
H–[CH₂–C(CH₃)=CH–CH₂]_n–OH	dolichols
H–[CH₂–C(CH₃)=CH–CH₂]_n–OH	polyprenols
H–[CH₂C(Me)=CHCH₂]_nOH	prenols
H–[CHOH]_n–C(=O)[CHOH]_m–H	ketoses
[(H₂O)_nH]⁺	cluster ion in mass spectrometry
H₃Si[OSiH₂]_nOSiH[OSiH₂OSiH₃]₂	siloxanes
H₃Si[OSiH₂]_nOSiH₃	siloxanes
H₃Si[SSiH₂]_nSSiH₃	silathianes
H₃S_n[OSnH₂]_nOSnH₃	stannoxanes
HA	Brønsted relation
HA	general acid catalysis
HB⁺	homoconjugation
HD	branching ratio
HDO	gaseous diffusion separator in atmospheric chemistry
HDO	heavy water
HL	extraction (equilibrium) constant
HL_aq	extraction (equilibrium) constant
H_nL	protonation constant
(HO)₂P(=O)(OR)	esters
[HOC(=NH₂)NH₂]⁺X⁻	uronium salts
HOC(=O)[CH(OH)]_nC(=O)OH	aldaric acids
HOCH₂[CH(OH)]_nC(=O)OH	aldonic acids
HOCH₂[CH(OH)]_nCH₂OH	alditols
HOCR'=CR₂	enols
HON=C{[CH₂]_n}₂C=NOH	E, Z
HS_nH	polysulfanes
HTO	gaseous diffusion separator in atmospheric chemistry
L	formation constant
L	isostructural reaction
L	protonation constant
l'	syntectic reaction
l''	syntectic reaction
Li_xTiS₂	intercalation reaction
M	alkoxides
M	atom–molecule complex mechanism
M	dimeric ion in mass spectrometry
M	formation constant
M	isostructural reaction
M	protonated molecule in mass spectrometry
M	sialon
M⁻	charge-transfer reaction in mass spectrometry
M⁺	charge-transfer reaction in mass spectrometry
[M + H]⁺	protonated molecule in mass spectrometry
[M₂]⁺^.	dimeric ion in mass spectrometry
M²⁺	charge-transfer reaction in mass spectrometry
MgX₂	Grignard reagents
MH⁺	protonated molecule in mass spectrometry
ML_n	extraction (equilibrium) constant
ML_n	formation constant
ML_n	isostructural reaction
ML_n-1X	isostructural reaction
Mⁿ	extraction (equilibrium) constant
M–Si–Al–O–N	sialon
N⁺abcd	chirality centre
–N=CR₂	nitrile ylides
Nd³⁺	neodymium laser
Nd³⁺	solid state lasers
Ng	excimer lamp
Ng₂	excimer lamp
NHR	amides
N_nH_n+2	azanes
=NNR₂	hydrazonic acids
=NOR	hydroximic acids
=NR	amidines
=NR	diamidides
=NR	imidic acids
=NR	imidines
=NR	quinonimines (quinone imines)
NR	imines
NR	ylides
–NR–	diamidides
–NR–	imidines
(=NR)₂	sulfonediimines
NR₂	amides
NR₂	glycosylamines
–NR₂	sulfenamides
–NRNR₂	hydrazides
O=NN=CR₂	nitrosimines
O₂NN=CR₂	nitrimines
[–OSiR₂–]_n	silicones
O⁻–Z–O^.	semiquinones
P(=O)(NR₂)₃	phosphoramides
P(=O)(OH)(NR₂)₂	phosphoramides
P(=O)(OH)₂(NR₂)	phosphoramides
Pabc	chirality centre
PhX	selectivity factor, $S f$
P_nH_n+2	phosphanes
+R	cross-conjugation
R	acetals
R	aldehydes
R	alkoxides
R	alkyl groups
R	arsines
R	azomethines
R	bisecting conformation (eclipsing conformation)
R	bismuthines
R	carbene analogues
R	diazoamino compounds
R	diazoates
R	esters
R	ethers
R	hemiaminals
R	hemiketals
R	hydrazides
R	hydroperoxides
R	hydropolysulfides
R	imines
R	ketals
R	ketimines
R	ketones
R	ketoximes
R	organically modified silica
R	phosphines
R	polysulfides
R	selenenic acids
R	selenides
R	selenols
R	selenoxides
R	selones
R	silicones
R	steric effect
R	stibines
R	sulfenamides
R	sulfenic acids
R	sulfenyl groups
R	sulfenylium ions
R	sulfenyl radicals
R	sulfides
R	sulfones
R	sulfoxides
R	tellurides
R	thioacetals
R	thioethers
R	thioketones
R	thioketone S-oxides
R	thiols
R⁻	common-ion effect (on rates)
-R	cross-conjugation
R'	acetals
R'	alkoxyamines
R'	carbamates
R'	diazoamino compounds
R'	enols
R'	hemiacetals
R'	imines
R'	nitrones
R'	ortho esters
R'	oxime O-ethers
R'	Schiff bases (Schiff's bases)
R'	thioacetals
R'	thiohemiacetals
R'	trioxides
R'	urethanes (urethans)
R'₂C=NR	imines
R'C(=O)(OR)	esters
R'C(=O)(SR)	esters
R'C(=S)(OR)	esters
R'S(=O)₂(OR)	esters
(R'S)₂C(=O)	esters
R–[S]_n–R	polysulfides
R⁺	attachment
R⁺	common-ion effect (on rates)
R⁺	ion pair return
R¹	E, Z
R¹^.	α-cleavage (alpha-cleavage)
R¹COOR²	moiety
R¹R²C(=C=C)_n=CR³R⁴	E, Z
R¹R²C=CR³R⁴	E, Z
R¹R²C=NOH	E, Z
R²	E, Z
R₂AsH	arsines
R₂BiH	bismuthines
R₂BOH	borinic acids
R₂C:	alkylidenes
R₂C^.⁺	carbene radical cations
R₂C^.–O⁻	ketyls
R₂C^.–OH	ketyls
R₂C(OH)–(OH)R₂	pinacols
R₂C(OH)NR₂	hemiaminals
R₂C(OH)OR	hemiketals
R₂C(OH)OR'	hemiacetals
R₂C(OR')(SR')	thioacetals
R₂C(OR')NR₂	hemiaminals
R₂C(OR')SH	thiohemiacetals
R₂C(OR)₂	ketals
R₂C(SR')₂	thioacetals
R₂C(SR')OH	thiohemiacetals
R₂C(SR')SH	thiohemiacetals
R₂C⁺–CR=C⁻R	vinyl carbenes
R₂C=	hydrocarbylidene groups
R₂C=C:	vinylidenes
R₂C=C⁺–R	vinylic cations
R₂C=C=C=CR₂	cumulenes
R₂C=C=CR₂	allenes
R₂C=C=NR	ketenimines
R₂C=C=O	ketenes
R₂C=CRC:R	vinyl carbenes
(R₂C=N:⁺)	nitrenium ions
R₂C=N^.	iminyl radicals
R₂C=N⁺	iminylium ions
R₂C=N⁺(O⁻)H	nitrones
R₂C=N⁺(O⁻)R'	nitrones
R₂C=N⁺H₂X⁻	onium compounds
R₂C=N⁺R₂	iminium compounds
R₂C=N⁺R₂Y⁻	quaternary ammonium compounds
R₂C=N⁺R–C⁻R₂	ylides
R₂C=NNHC(=O)C(=O)NH₂	semioxamazones
R₂C=NNHC(=O)NH₂	semicarbazones
R₂C=NNR₂	hydrazones
R₂C=N–O^.	iminooxy (iminoxy) radicals
R₂C=NOH	ketoximes
R₂C=NOH	oximes
R₂C=NOR'	oxime O-ethers
R₂C=NR'	ketimines
R₂C=NR'	Schiff bases (Schiff's bases)
R₂C=O	ketones
R₂C=O⁺–Y⁻	oxonium ylides
R₂C=S	thioketones
R₂C=S=O	thioketone S-oxides
R₂C=Se	selones
R₂C=SO₂	sulfenes
R₂CH–O^.	ketyls
R₂CML_n	metal–carbene complexes
R₂C⁻–O^.	ketyls
R₂C^…	alkylidynes
R₂C^…⁻	carbene radical anions
R₂Ge:	carbene analogues
R₂Ge:	germylidenes
R₂Mg	Grignard reagents
(R₂N:⁺)	nitrenium ions
R₂N^.	aminyl radicals
R₂N^.⁺–O⁻	aminoxyl radicals
(R₂N)₄C	ortho amides
R₂N[CH=CH]_nCH=N⁺R₂	cyanine dyes
R₂N⁺=CH[CH=CH]_nNR₂	cyanine dyes
R₂NC(=O)OH	urethanes (urethans)
R₂NC(=O)OR'	urethanes (urethans)
R₂NCR=CR₂	enamines
R₂NNO	nitrosamines
R₂N–O⁻	aminoxides
R₂N–O^.	aminoxyl radicals
R₂N–OH	aminoxides
R²O	moiety
R₂O⁺–C⁻R₂	oxonium ylides
R₂Pb:	carbene analogues
R₂Pb:	plumbylidenes
R₂PH	phosphines
R₂POH	amides
R₂S(=O)=NR	sulfoximides
R₂S=O	sulfoxides
R₂SbH	stibines
R₂Se(=O)₂	selenones
R₂Se=O	selenoxides
R₂Si:	carbene analogues
R₂Sn:	carbene analogues
R₂Sn:	stannylidenes
R₂Te(=O)₂	tellurones
R₂X⁺	halonium ions
R₂Z⁺–N⁻R	imides
R³	E, Z
R₃As	arsines
R₃Bi	bismuthines
R₃C–C(Y)=X	bisecting conformation (eclipsing conformation)
R₃N	amine imides
R₃N⁺–C⁻R₂	ylides
R₃P	phosphines
R₃P⁺–C⁻R₂	phosphonium ylides
R₃P⁺–O⁻	phosphine oxides
R₃P=CR₂	phosphonium ylides
R₃P=O	phosphine oxides
R₃S⁺	sulfonium compounds
R₃Sb	stibines
R₃Si–	silyl groups
R₃Si^.	silyl radicals
R₃SiC(=O)R	ketones
R₃SiOH	silanols
R₃SiOR	ethers
R₃Y⁺–N⁻R	imides
R⁴	E, Z
[R₄As]⁺X⁻	arsonium compounds
R₄P^.	phosphoranyl radicals
[R₄P⁺]X⁻	phosphonium compounds
[R₄Sb]⁺X⁻	stibonium compounds
R–As	arsanylidenes
RAs:	carbene analogues
RAsH₂	arsines
RB:	boranylidenes
RB:	carbene analogues
RB(OH)₂	boronic acids
RBiH₂	bismuthines
R–C:–CH₂C(=NR)R	imino carbenes
RC(=NH)–	imidoyl carbenes
RC(=NOH)NO	nitrosolic acids
RC(=NOH)NO₂	nitrolic acids
RC(=NR)(OH)	imidic acids
RC(=NR)C:–R	imidoyl carbenes
RC(=NR)NRC(=NR)R	diamidides
[RC(=O)]₂NR	diacylamines
RC(=O)H	aldehydes
RC(=O)NHNH₂	hydrazides
RC(=O)NHOH	hydroxamic acids
RC(=O)OH	oxoacids
RC(=O)SH	thiocarboxylic acids
RC(=S)H	thioaldehydes
RC(=S)OH	thiocarboxylic acids
RC(=S)SH	thiocarboxylic acids
RC(=S=O)H	thioaldehyde S-oxides
RC(NH₂)₃	ortho amides
RC(NHNH₂)₂=NNH₂	hydrazidines
RC(OH)=C(OH)C(=O)R	reductones
RC(OH)=NNH₂	hydrazonic acids
RC(OH)=NOH	hydroximic acids
RC(OH)₃	ortho acids
RC(OR')₃	ortho esters
RCH=C=O	ynols
RCH=NN=CHR	aldazines
RCH=NOH	aldoximes
RCH=NR	aldimines
RCH=NR	imines
RCML_n	metal–carbyne complexes
R–C–R	bisecting conformation (eclipsing conformation)
RC≡	hydrocarbylidyne groups
R–C≡C⁻	umpolung
'R–C≡C⁺	umpolung
RC≡CH	acetylides
RC≡CNR₂	ynamines
RC≡COH	ynols
RC≡CR	alkynes
R–C≡CX	umpolung
RC≡N	carbonitriles
RC≡N	nitriles
RC≡N⁺–C⁻R₂	ylides
RC≡N⁺N⁻–R	ylides
R–C≡N⁺–Y⁻	nitrilium betaines
RC≡NH⁺	onium compounds
RC≡O⁺	onium compounds
RH	diazoamino compounds
R_kE(=O)_l(OH)_m	acyl groups
R_kE(=O)_l(OH)_m	acyl species
R_kE(=O)_l(OH)_m	amides
R_kE(=O)_l(OH)_m	anilides
R_kE(=O)_l(OH)_m	cyclic acid anhydrides (cyclic anhydrides)
R_kE(=O)_l(OH)_m	esters
R_kE(=O)_l(OH)_m	hydrazides
R_kE(=O)_l(OH)_m	hydrazonic acids
R_kE(=O)_l(OH)_m	hydroxamic acids
R_kE(=O)_l(OH)_m	hydroximic acids
R_kE(=O)_l(OH)_m	imidic acids
RMgX	Grignard reagents
R_mX	ylides
R_mX⁺–C⁻R₂	ylides
R_mX⁺–Y⁻	ylides
R_mX⁺–Y⁻R_n	ylides
R_mX=Y	ylides
R_mX=YR_n	ylides
RN:	amine imides
RN:	carbene analogues
RN⁺≡C⁻	isocyanides
RN⁺≡N	diazonium salts
RN=	imides
RN=	imino carbenes
RN=C=O	isocyanates
RN=C=S	isothiocyanates
RN=C=S	mustard oils
RN=C=Se	isoselenocyanates
RN=CR₂	imines
RN=N^.	diazenyl radicals
RN=N⁺	diazonium salts
RN=NNHR'	diazoamino compounds
RN=N–NR₂	diazoamino compounds
RN=NOH	diazoates
RN=NO⁻M⁺	diazoates
RN=S(=O)₂	sulfimides
RN=S(=O)₂	sulfonylamines
RN=S=O	sulfinylamines
RN²⁻	imides
RN₂⁺Y⁻	diazonium salts
RNC	isocyanides
R–NCO	esters
R_nE(=O)OH	amidines
R_nE(NR₂)_m	amides
R_nE(OH)_m	amides
RNHNO	nitrosamines
R^o	steric effect
RO–	glycosides
(RO)₃Si–CH=CH₂	chemical functionality
(RO)_aSi(B)_b(C)_c(D)_d	organically modified silica
RO⁺	oxenium ions
RO⁺	oxylium ions
ROC(=S)SH	xanthic acids
ROCN	esters
ROH	alkoxides
ROM	alkoxides
RON=C:	fulminates
RO–NO	Barton reaction
ROOH	hydroperoxides
ROOOR'	trioxides
ROOR	peroxides
ROR	ethers
R^oY	steric effect
RP:	carbene analogues
RP:	phosphanylidenes
RP(=O)(NHNH₂)₂	hydrazides
RP(=O)(OH)₂	oxoacids
RPH₂	phosphines
RS–	glycosides
RS–	sulfenyl groups
RS^.	sulfenyl radicals
RS(=NH)₂(OH)	imidic acids
RS(=NH)₂=NH₂	sulfonamidines
RS(=NR)₂R	sulfonediimines
RS(=NR)NR₂	sulfinamidines
RS(=O)(=NNH₂)OH	hydrazonic acids
RS(=O)(=NOH)OH	hydroximic acids
RS(=O)=NH₂	sulfonamidines
RS(=O)₂NHC(=O)R	diacylamines
RS(=O)₂NHNH₂	hydrazides
RS(=O)₂NR'₂	sulfonamides
RS(=O)₂OS(=O)₂R'	sulfonic anhydrides
RS(=O)₂R	sulfones
RS(=O)NR₂	sulfinamides
RS(=O)OH	sulfinamides
RS(=O)OH	sulfinamidines
RS(=O)OS(=O)R	sulfinic anhydrides
RS⁺	sulfenylium ions
RS₂H	hydropolysulfides
RS₂R	polysulfides
RS₃H	hydropolysulfides
RSb:	carbene analogues
RSb:	stibanylidenes
RSbH₂	stibines
RSe–	glycosides
RSe(=O)₂OH	selenonic acids
RSe(=O)OH	seleninic acids
RSeH	selenols
RSeOH	selenenic acids
RSeR	selenides
RSH	thiols
RS_nH	hydropolysulfides
RSOH	amides
RSOH	sulfenamides
RSOH	sulfenic acids
RSR	sulfides
RSR	thioethers
RTeR	tellurides
RX	common-ion effect (on rates)
RY	steric effect
Sb_nH_n+2	stibanes
(SiH)_2n(NH)_3n	silasesquiazanes
(SiH)_2nO_3n	silasesquioxanes
(SiH)_2nS_3n	silasesquithianes
Si_nH_2n+1OH	silanols
Si_nH_2n+2	silanes
Sm	semiconductor-metal transition
Sm²⁺S²⁻	valence transition
(Sm³⁺+e⁻)S²⁻	valence transition
SmS	semiconductor-metal transition
S_n	hydropolysulfides
ThO₂	solute-volatilization interference in flame spectroscopy
[TS]^‡	kinetic isotope effect
X	bisecting conformation (eclipsing conformation)
X	charge-transfer reaction in mass spectrometry
X	cross-conjugation
X	dipolar compounds
X	dual substituent-parameter equation
X	extended Hammett equation
X	extrusion transformation
X	halonium ions
X	Hammett equation (Hammett relation)
X	insertion
X	isostructural reaction
X	phosphonitriles
X	protonated molecule in mass spectrometry
X	umpolung
X⁻	common-ion effect (on rates)
X:–C=Z	dipolar compounds
X'	telomerization
X''	telomerization
X⁺	common-ion effect (on rates)
X⁺	ion pair
X⁺	ylides
X⁺=C–Z⁻	dipolar compounds
X⁺Y⁻	ion pair
X⁺–Y–Z⁻	dipolar compounds
X⁻=N⁺=Z	dipolar compounds
X⁻=N–Z⁺	dipolar compounds
X=Y⁺–Z⁻	dipolar compounds
X⁻=Y–Z⁺	dipolar compounds
X₂	excimer lamp
X₂	pseudohalogens
[X₂PN]_n	phosphonitriles
Xabc₂	pro-R, pro-S
(XC₂H₂C₂H₂)₂NR	mustards
(XC₂H₂C₂H₂)₂S	mustards
XC₆H₄GY	cross-conjugation
XC₆H₄Y	Hammett equation (Hammett relation)
XH⁺	protonated molecule in mass spectrometry
X–N=Z	dipolar compounds
X⁻–Y⁺=Z	dipolar compounds
XZ	insertion
X≡N⁺–Z⁻	dipolar compounds
Y	dipolar compounds
Y	extrusion transformation
Y	imides
Y	insertion
Y	steric effect
Y	ylides
Y⁻	ion pair
Y⁻	ylides
YBa₂Cu₃O_7-x	superconducting transition
Z	dipolar compounds
Z	extrusion transformation
Z	imides
Z	insertion
Z⁻	ion pair return
Z=X⁺–Y⁻R_n	ylides
Z⁻–X⁺=YR_n	ylides
α	syntectic reaction