research article distribution of picric acid into various...

Hindawi Publishing CorporationJournal of ChemistryVolume 2013 Article ID 869506 4 pageshttpdxdoiorg1011552013869506

Research ArticleDistribution of Picric Acid into Various Diluents

Yoshihiro Kudo1 Yuu Takahashi2 and Shoichi Katsuta1

1 Graduate School of Science Chiba University 1-33 Yayoi-cho Inage-ku Chiba 263-8522 Japan2Department of Chemistry Faculty of Science Chiba University 1-33 Yayoi-cho Inage-ku Chiba 263-8522 Japan

Correspondence should be addressed to Yoshihiro Kudo iakudofacultychiba-ujp

Received 30 May 2013 Accepted 5 August 2013

Academic Editor Eri Yoshida

Copyright copy 2013 Yoshihiro Kudo et alThis is an open access article distributed under the Creative CommonsAttribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

Extraction constants defined as 119870ex = [HPic]o[H+][Picminus] for picric acid (HPic) into ten diluents were spectrophotometrically

determined at 298K where the subscript ldquoordquo refers to an organic (o) phase which is composed of the diluent Their values for theHPic extraction into benzene and chloroform were fairly consistent with those reported before From the 119870ex values distributionconstants (119870DHPic) of HPic into the o phases were estimated using the thermodynamic relation 119870ex = 119870DHPic119870HPic where 119870HPiccorresponds to a protonation constant of Picminus in waterThereby contributions of functional groups such as ndashCl and ndashCH

3 involved

in the diluents molecules to 119870DHPic were discussed The same discussion was also applied for the distribution of the ion paircomposed of CdPic

2and 18-crown-6 ether into the diluents

1 Introduction

Picric acid (HPic) has been widely used for the source ofpairing anions in solvent extraction [1ndash5] application toselective sensors [6] sequential injection analysis with it [7]its separation science [8 9] theoretical study for its partition[10] its distribution into ionic liquids [11] and so on Alsomany authors have studied extraction and separation ofmanymetal ions by crown compounds from water (w) into variousdiluents [1ndash3 12ndash17] In particular the extraction data ofHPicare important for studying the extraction of easily hydrolyzedmetal ions such as Ag+ and Pb2+ by the compounds into thediluents [1 2 18] However few systematic studies of theHPicextraction have been reported [5]

In the present paper we systematically determined at298K extraction constants (119870exmolminus1 dm3) of HPic into tendiluents having lower polarities such as 119898-Xylene (mX)toluene (TE) bromobenzene (BBz) chlorobenzene (CBz)and 1-chlrorobutane (CBu) These diluents were selected onthe basis of the careful consideration by Takeda et al [3]From the 119870ex values distribution constants (119870DHA) of HPicbetween thew andorganic (o) phases or the diluentswere alsocalculatedMoreover contributions of functional groups con-stituting the diluents molecules to119870DHA were discussedThesame discussion was applied for the distribution of the ionpair of CdPic

2with 18-crown-6 ether (18C6) into the diluents

2 Materials and Methods

21 Materials Picric acid (995 HPicsdot119909H2O) was pur-

chased fromWako Pure Chemical Industries Japan Sodiumhydroxide (97 Kanto Chemical Co Ltd Japan) wasused without further purification Its purity was determinedby acid-base titration with potassium hydrogen phthalate(guaranteed pure reagent GR 999 to 1002 Kanto) Thechemicals HPicsdot119909H

2O were dissolved in water and then its

concentration was determined by acid-base titration withan aqueous NaOH solution of 01mol dmminus3 Commerciallyavailable diluents (all GR grades Wako and Kanto) werewashed three times with water and kept under the conditionssaturated with water Other chemicals were of GR grade Atap water was distilled once with the still of the stainlesssteel and then was purified by passing through the Autopuresystem (YamatoMillipore type WT101 UV) This water wasemployed for preparation of all aqueous solutions

22 Extraction Procedures andDataHandling AqueousHPicsolutions of (01

5ndash34) times 10minus3mol dmminus3 and diluents were

mixed at equivalent volume (12 cm3) in glass tubes of about30 cm3 and then these stoppered glass tubes were vigorouslyshaken by hand for 1 minute The tubes were agitated for2 h by a shaker with water-bath thermostated at 298K andthen in order to separate the two phases centrifuged for

2 Journal of Chemistry

25 30 35 40pH

logD

Pic

minus3

minus2

minus1

0

Figure 1 Plots of log119863Pic versus pH for six diluents Circle DCEtriangle DCM full circle CBu diamond BBz inverted triangle Bzsquare mX A broken line is the regression one for the DCE systembased on (2) log119863Pic = 2489ndashpHndashlog(1+386times10minuspH) at119877 = 0998

7 minutes The pH values of the w phases separated weremeasured at 298K pH readings were in the range of 257to 410 A Horiba pHion meter (type F-23) equipped witha glass electrode (Horiba type 9615-10D) was employed forthe pH measurements While the o phases or the diluentsseparated were transferred into other glass tubes and theaqueous NaOH solutions of 01mol dmminus3 were added tothem volume ratios (119881o119881) of the separated o phases againstthe added aqueous solutions with NaOH were 11 12 1415 18 110 112 or 125 As similar to the above procedurethe amounts of HPic in the o phases were back-extractedinto the aqueous NaOH solutions Using a 1 cm quartzcell concentrations of Picminus in these aqueous solutions weredetermined spectrophotometrically at 3550 nm and 298Kwhere a spectrophotometer used was of a Hitachi U-2001type The operation of the back-extraction was repeated insome cases

These Picminus concentrations which were determined at3550 nm due to the absorption of Picminus were assumed toequal the concentrations [HPic]o of HPic in the o phasesHere the subscript ldquoordquo denotes the o phase From these valuesand total concentrations [HPic]t of HPic distribution ratios119863Pic for Picminus were calculated assuming that [HPic]o ≫[Picminus]o + [(HPic)

2]o [19] and then using the equation 119863Pic =

[HPic]o([HPic]t minus [HPic]o) (see Section 31)As a software for the analysis of the plots of log119863Pic versus

pH (see Figure 1) a KaleidaGraph (ver 3501 Hulinks IncTokyo) was used

3 Results and Discussion

31 A Concise Theoretical Treatment of Extraction EquilibriaWeassumedhere the following equilibriaH++Aminus 999445999468 HAandHA 999445999468 HAo for the overall extraction equilibrium of which

the constant was expressed as 119870ex = [HA]o[H+][Aminus] For

this extraction system [9 10 19] the distribution ratio wasdefined as

119863A =[HA]o[Aminus] + [HA]

=119870ex [H

+]

1 + 119870HA [H+] (1)

Then taking logarithms of both sides the following equationwas given

log119863A = log119870ex minus pH minus log (1 + 119870HA [H+

])

= log119870ex minus pH minus log (1 + 119870HA10minuspH)

(2)

Assuming that the119870HA values are a constant in a given exper-imental pH range (see Section 22) then we can immediatelyobtain the log119870ex value from the plot of log119863A versus pHActually the 119870HA values which were averaged for all thevalues of ionic strength (119868) were employed for the analysis ofthe plots where 119868 = (12)([H+]+ [Aminus]) asymp [H+] Additionallythe log119870DHA value can be estimated from the thermo-dynamic relation log119870ex = log119870DHA+log119870HA Also (2) canapproximate to log119863A asymp log119870exminus pH in the present experi-mental ranges of pH (see Section 22)

32 Determination of 119870ex and 119870DHPic Figure 1 shows exam-ples for plots of log119863A versus pH at Aminus = Picminus Thus theplots yielded linear relationships between log119863A and pHThe same is also true of the HPic extraction systems withthe other four diluents The extraction data thus obtained aresummarized in Table 1 The log119870ex values of the extractioninto benzene Bz and chloroform CF were in accord withthose [1 2] reported before by Takeda et al Although themeasuring temperature was not described the log119870ex value(=228 [10]) estimated previously for the dichloromethaneDCM system was also close to our value (=2462) From thelog119870HPic values in Table 1 one can see easily that differencesamong the present 119868 values the average 119868 ones have noobjection to comparisons among the 119870ex values or compo-nent equilibrium constants except for the cyclohexane cHexsystem [8]

33 Extraction Abilities of the Diluents for HPic According tothe relation log119870ex = log119870DHA+log119870HA the extraction abil-ity of the diluents employed for HPic is obviously controlledby the log119870DHA values (see Table 1) This is supported by thefollowing facts A plot of log119870ex versus log119870DHPic for the tendiluents gave a straight line with the slope of 100

1and the

intercept of 0584at the correlation coefficient (119877) of 0999

This intercept was also in good agreement with the log119870HPicvalues listed in Table 1 within the experimental errors ofplusmn001

34 For Interaction of the Diluents Molecules with HPicThe log119870DHA values were in the order cHex ≪ CBu ltCF lt oDCBz lt BBz CBz lt Bz lt DCM TE le DCE lt mX(see Table 1 for these abbreviations) This order shows thatan interaction with HPic becomes strengthened by goingfrom cHex to mX We divide here the order into (cHex ≪)

Journal of Chemistry 3

Table 1 Extraction constants for HPic into various diluents and their component equilibrium constants (119870HA 119870DHA) at 298K

Diluentsa 119868bmol dmminus3 log 119870ex

c log KDHA log 119870HAde

DCE 78 times 10minus4

2489 plusmn 0006 190 plusmn 001 059oDCBz 10 times 10

minus3

2170 plusmn 0002 159 plusmn 001 058DCM 84 times 10

minus4

2462 plusmn 0002 188 plusmn 001 059CBu 10 times 10

minus3

1474 plusmn 0004 089 plusmn 001 058CBz 85 times 10

minus4

2310 plusmn 0002 172 plusmn 001 059BBz 87 times 10

minus4

2300 plusmn 0007 172 plusmn 001 059CF 37 times 10

minus4

1941 plusmn 0003 1940f

1347 plusmn 0006 1650

f0594 plusmn 0005 029

0

fg

cHexh 10i 066 minus016 082Bz 81 times 10

minus4

2396 plusmn 0005 2393j

181 plusmn 001 2103

j 059 0290

jg

TE 63 times 10minus4

2473 plusmn 0006 188 plusmn 001 059mX 79 times 10

minus4

2552 plusmn 0005 197 plusmn 001 059aDCE 12-dichloroethane oDCBz o-dichlorobenzene DCM dichloromethane CBu 1-chlorobutane CBz chlorobenzene BBz bromobenzene CFchloroform cHex cyclohexane Bz benzene TE toluene mX m-xylene These diluents are lined up downwards from the high-polar DCE to the low-polarmX bAverage values of 119868 in aqueous solutions c119870exmolminus1 dm3 dAverage values evaluated at 119868 and expressed by 119870HAmol dmminus3 eErrors of all the log119870HAvalues evaluated here were plusmn001 except for the CF system fReference [2] gLog119870HPic value at (Imol dmminus3) = 01 See [21] hReference [8] iConcentration ofHCl jReference [1]

oDCBz lt BBz CBz lt Bz lt TE lt mX for aromatic diluentsand CBu lt CF ltDCM leDCE for aliphatic diluents and thenwill examine these orders in more detail

The log119870DHA values were in the order Bz lt TE lt mX(Table 1)This fact indicates that substitution of ndashH by ndashCH

3

increases the interaction of the diluents molecules with HPicSimilar results were obtained for the substitution of ndashCl orndashBr by ndashCH

3 namely CBz or BBz lt TE and oDCBz lt mX

although the position of the functional group in the lattercase differs from each other On the other hand those of ndashClby ndashCH

2CH2CH3and ndashCH

2CH3decreased the interaction

withHPicThe corresponding examples were DCM (ClCH2ndash

Cl) ≫ CBu (ClCH2ndashCH2CH2CH3) and DCE (ClCH

2CH2ndash

Cl) ≫ CBu (ClCH2CH2ndashCH2CH3) respectively Also the

substitution of ndashH by ndashCl decreased their interaction Theseexamples were DCM gt CF and Bz gt CBz gt oDCBz Like therelation between Bz and CBz the same was also true of thatbetween Bz and BBzThe above results indicate that the func-tional groups constituting the diluents molecules strengthenthe interaction with HPic in the order of ndashCH

2CH2CH3

ndashCH2CH3≪ ndashCl ndashBr lt ndashH le ndashCH

3

The case of cHex ≪ Bz suggests that the substitution ofndashCH2CH2ndash by ndashCH=CHndash strengthens the interaction with

HPic while there was no difference in the interaction withHPic between ndashCl and ndashBr and accordingly that in log119870DHAbetween CBz and BBz (Table 1)

35 Application for the Distribution of Ion Pairs with 18C6The log119870DMLA2 values reported previously [20] at MLA

2=

Cd(18C6)Pic2were in the order Bz (minus618) ≪ TE (minus485) lt

CBu (minus448) lt mX (minus413) ≪ CBz (minus270) lt CF (minus262) ltDCE (minus253) le DCM (minus252) Comparing these values withthe log119870DHPic ones for given diluents we can easily see thatCd(18C6)Pic

2more weakly (or more strongly) interacts with

the diluents (or water) molecules than HPic does The highpolarity [20] of the Cd(18C6)Pic

2structure is also supported

by this comparison Similarly the order was divided intoBz≪ TE lt mX≪ CBz for aromatic diluents and CBu≪ CFlt DCE le DCM for aliphatic diluents

The same analysis as that described in Section 34 gavethe order of ndashH le ndashCH

3≪ ndashCl for the former while it did

that of ndashCH2CH2CH3 ndashCH

2CH3≪ ndashCl le ndashH for the latter

A comparison of these orders with that for the HPic distri-bution system indicates that the interaction of the aromaticdiluents molecules with Cd(18C6)Pic

2differs from that with

HPic while the interaction of the aliphatic diluents ones isessentially similar to it Especially it is suggested that thesubstitution of ndashH by ndashCl in the aromatic diluents moleculesor altering Bz into CBz strengthens the interaction withCd(18C6)Pic

2 being contrary to theHPic systemThe same is

true of the substitution of ndashCH3by ndashCl altering TE into CBz

4 Conclusions

The119870ex and119870DHPic values for theHPic extraction into the tenlow-polar diluents were systematically determined at 298KThe magnitudes of the former constants were exclusivelycontrolled by those of the latter ones from analyzing theirthermodynamic relation with 119870HPic The contributions ofthe functional groups constituting the diluents moleculesto 119870DHPic were clarified subsystematically That is it wasdemonstrated that the interaction of HPic with the diluentsmolecules is strengthened by introducing a methyl group intheirmolecules Also the contributions to119870DCd(18C6)Pic2werepartly different from those to119870DHPicThe authors cannot nowexplain essential meanings of such contributions

Conflict of Interests

The authors do not have any possible conflict of interests withany trademarks mentioned in the paper Of course they donot receive any financial gains from the two companies at all


References

[1] Y Takeda andH Kato ldquoThe solvent extraction of bivalentmetalpicrates by 15-crown-5 18-crown-6 and dibenzo-18-crown-6rdquoBulletin of the Chemical Society of Japan vol 52 no 4 pp 1027ndash1030 1979

[2] Y Takeda and M Nishida ldquoSolvent extraction of various metalpicrates with benzo-18-crown-6 into CHCl

3rdquo Bulletin of the

Chemical Society of Japan vol 62 no 5 pp 1468ndash1471 1989[3] Y Takeda R Taguchi and S Katsuta ldquoStudy on solute-solvent

and solute-solute interactions for the dibenzo-24-crown-8-alkali metal picrate extraction systemrdquo Journal of MolecularLiquids vol 115 no 2-3 pp 139ndash147 2004

[4] J Rais ldquoIndividual extraction constants of univalent ions inthe system water-nitrobenzenerdquo Collection of CzechoslovakChemical Communications vol 36 no 9 pp 3253ndash3262 1971

[5] L M Ferreira and E Lopes ldquoSolvent extraction of picric acidfrom aqueous solutionsrdquo Journal of Chemical and EngineeringData vol 41 no 4 pp 698ndash700 1996

[6] M A F Elmosallamy ldquoNew highly selective picrate sensorsbased on charge-transfer complexesrdquo Analytical Sciences vol20 no 2 pp 285ndash290 2004

[7] J Skrlıkova V Andruch H Skelnarova P Chocholous PSolich and I S Balogh ldquoA novel dual-valve sequential manifold(DS-SIA) for automated liquid-liquid extraction Applicationfor the determination of picric acidrdquo Analytica Chimica Actavol 666 no 1-2 pp 55ndash61 2010

[8] T Sekine Y Katayama YWakabayashi andHNaganawa ldquoSol-vent extraction of picric acid from acid aqueous solutions intocyclohexane with trioctylphosphine oxide and trioctylaminerdquoSolvent Extraction and Ion Exchange vol 7 no 1 pp 73ndash861989

[9] H Uslu ldquoSeparation of picric acid with trioctyl amine (TOA)extractant in diluentsrdquo Separation Science and Technology vol46 no 7 pp 1178ndash1183 2011

[10] V Pradines S Despoux C Claparols et al ldquoPartition of dis-sociable compounds in two-phase liquid systems a theoreticaland experimental studyrdquo Journal of Physical Organic Chemistryvol 19 no 6 pp 350ndash358 2006

[11] S Katsuta ldquoDistribution behavior of neutral and anionic com-pounds in ionic liquidwater biphasic systemsrdquoBunseki Kagakuvol 62 no 4 pp 297ndash315 2013 (Japanese)

[12] T G Levitskaia L Maya G J van Berkel and B A MoyerldquoAnion partitioning and ion-pairing behavior of anions in theextraction of cesium salts by 45

10158401015840

-bis(tert-octylbenzo)dibenzo-24-crown-8 in 12-dichloroethanerdquo Inorganic Chemistry vol 46no 1 pp 261ndash272 2007

[13] Y Kikuchi andY Sakamoto ldquoComplex formation of alkalimetalions with 18-crown-6 and its derivatives in 12-dichloroethanerdquoAnalytica Chimica Acta vol 403 no 1-2 pp 325ndash332 2000

[14] P Vanura and E Makrlık ldquoExtraction of cesium withbis[undecahydro-7 8-dicarbaundeca-borato(2-)]cobaltate(1-)in the presence of 18-crown-6rdquo Collection of CzechoslovakChemical Communications vol 63 no 12 pp 2001ndash2008 1998

[15] L Olsher M G Hankins Y D Kim and R A Bartsch ldquoAnioneffect on selectivity in crown ether extraction of alkali metalcationsrdquo Journal of the American Chemical Society vol 115 no8 pp 3370ndash3371 1993

[16] A Sadakane T Iwachido and K Toei ldquoThe extraction ofalkali metal picrates with dibenzo-18-crown-6rdquo Bulletin of theChemical Society of Japan vol 48 no 1 pp 60ndash63 1975

[17] Y Kudo J Usami S Katsuta and Y Takeda ldquoOn the differencebetween ion-pair formation constants of crown ether-complexions with picrate ion in water determined by solvent extractionand by potentiometryrdquo Journal ofMolecular Liquids vol 123 no1 pp 29ndash37 2006

[18] Y Kudo J Usami S Katsuta and Y Takeda ldquoSolvent extractionof silver picrate by 3119898-crown-119898 ethers (119898 = 5 6) and its mono-benzo-derivative from water into benzene or chloroform elu-cidation of an extraction equilibrium using component equi-librium constantsrdquo Talanta vol 62 no 4 pp 701ndash706 2004

[19] M Tanaka Yobai-Chusyutsu no Kagaku Kyoritsu-SyuppanTokyo Japan 1979 (Japanese)

[20] Y Kudo N Horiuchi S Katsuta and Y Takeda ldquoExtraction ofcadmium bromide and picrate by 18-crown-6 ether into variousless-polar diluents analysis of overall extraction equilibriabased on their component equilibria with formation of their ionpairs in waterrdquo Journal of Molecular Liquids vol 177 pp 257ndash266 2013

[21] G KortumWVogel andKAndrussowDissociationConstantsof Organic Acids in Aqueous Solutions IUPAC Section of Ana-lytical Chemistry Commission on Electrochemical Data But-terworths London UK 1961

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Applied ChemistryJournal of



Theoretical ChemistryJournal of


Journal of

Spectroscopy

Analytical ChemistryInternational Journal of


Journal of


Quantum Chemistry


Organic Chemistry International

ElectrochemistryInternational Journal of



CatalystsJournal of


25 30 35 40pH

logD

Pic

minus3

minus2

minus1

0

Figure 1 Plots of log119863Pic versus pH for six diluents Circle DCEtriangle DCM full circle CBu diamond BBz inverted triangle Bzsquare mX A broken line is the regression one for the DCE systembased on (2) log119863Pic = 2489ndashpHndashlog(1+386times10minuspH) at119877 = 0998

7 minutes The pH values of the w phases separated weremeasured at 298K pH readings were in the range of 257to 410 A Horiba pHion meter (type F-23) equipped witha glass electrode (Horiba type 9615-10D) was employed forthe pH measurements While the o phases or the diluentsseparated were transferred into other glass tubes and theaqueous NaOH solutions of 01mol dmminus3 were added tothem volume ratios (119881o119881) of the separated o phases againstthe added aqueous solutions with NaOH were 11 12 1415 18 110 112 or 125 As similar to the above procedurethe amounts of HPic in the o phases were back-extractedinto the aqueous NaOH solutions Using a 1 cm quartzcell concentrations of Picminus in these aqueous solutions weredetermined spectrophotometrically at 3550 nm and 298Kwhere a spectrophotometer used was of a Hitachi U-2001type The operation of the back-extraction was repeated insome cases

These Picminus concentrations which were determined at3550 nm due to the absorption of Picminus were assumed toequal the concentrations [HPic]o of HPic in the o phasesHere the subscript ldquoordquo denotes the o phase From these valuesand total concentrations [HPic]t of HPic distribution ratios119863Pic for Picminus were calculated assuming that [HPic]o ≫[Picminus]o + [(HPic)

2]o [19] and then using the equation 119863Pic =

[HPic]o([HPic]t minus [HPic]o) (see Section 31)As a software for the analysis of the plots of log119863Pic versus

pH (see Figure 1) a KaleidaGraph (ver 3501 Hulinks IncTokyo) was used

3 Results and Discussion

31 A Concise Theoretical Treatment of Extraction EquilibriaWeassumedhere the following equilibriaH++Aminus 999445999468 HAandHA 999445999468 HAo for the overall extraction equilibrium of which

the constant was expressed as 119870ex = [HA]o[H+][Aminus] For

this extraction system [9 10 19] the distribution ratio wasdefined as

119863A =[HA]o[Aminus] + [HA]

=119870ex [H

+]

1 + 119870HA [H+] (1)

Then taking logarithms of both sides the following equationwas given

log119863A = log119870ex minus pH minus log (1 + 119870HA [H+

])

= log119870ex minus pH minus log (1 + 119870HA10minuspH)

(2)

Assuming that the119870HA values are a constant in a given exper-imental pH range (see Section 22) then we can immediatelyobtain the log119870ex value from the plot of log119863A versus pHActually the 119870HA values which were averaged for all thevalues of ionic strength (119868) were employed for the analysis ofthe plots where 119868 = (12)([H+]+ [Aminus]) asymp [H+] Additionallythe log119870DHA value can be estimated from the thermo-dynamic relation log119870ex = log119870DHA+log119870HA Also (2) canapproximate to log119863A asymp log119870exminus pH in the present experi-mental ranges of pH (see Section 22)

32 Determination of 119870ex and 119870DHPic Figure 1 shows exam-ples for plots of log119863A versus pH at Aminus = Picminus Thus theplots yielded linear relationships between log119863A and pHThe same is also true of the HPic extraction systems withthe other four diluents The extraction data thus obtained aresummarized in Table 1 The log119870ex values of the extractioninto benzene Bz and chloroform CF were in accord withthose [1 2] reported before by Takeda et al Although themeasuring temperature was not described the log119870ex value(=228 [10]) estimated previously for the dichloromethaneDCM system was also close to our value (=2462) From thelog119870HPic values in Table 1 one can see easily that differencesamong the present 119868 values the average 119868 ones have noobjection to comparisons among the 119870ex values or compo-nent equilibrium constants except for the cyclohexane cHexsystem [8]

33 Extraction Abilities of the Diluents for HPic According tothe relation log119870ex = log119870DHA+log119870HA the extraction abil-ity of the diluents employed for HPic is obviously controlledby the log119870DHA values (see Table 1) This is supported by thefollowing facts A plot of log119870ex versus log119870DHPic for the tendiluents gave a straight line with the slope of 100

1and the

intercept of 0584at the correlation coefficient (119877) of 0999

This intercept was also in good agreement with the log119870HPicvalues listed in Table 1 within the experimental errors ofplusmn001

34 For Interaction of the Diluents Molecules with HPicThe log119870DHA values were in the order cHex ≪ CBu ltCF lt oDCBz lt BBz CBz lt Bz lt DCM TE le DCE lt mX(see Table 1 for these abbreviations) This order shows thatan interaction with HPic becomes strengthened by goingfrom cHex to mX We divide here the order into (cHex ≪)







minus3


minus4


minus3


minus4


minus4


minus4

1941 plusmn 0003 1940f

1347 plusmn 0006 1650

f0594 plusmn 0005 029

0

fg


minus4

2396 plusmn 0005 2393j

181 plusmn 001 2103

j 059 0290

jg



minus4




3




2CH2CH3and ndashCH




2CH2ndash



2CH2CH3


3




2=
















4 Conclusions





References















10158401015840




















Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of







minus3


minus4


minus3


minus4


minus4


minus4

1941 plusmn 0003 1940f

1347 plusmn 0006 1650

f0594 plusmn 0005 029

0

fg


minus4

2396 plusmn 0005 2393j

181 plusmn 001 2103

j 059 0290

jg



minus4




3




2CH2CH3and ndashCH




2CH2ndash



2CH2CH3


3




2=
















4 Conclusions





References















10158401015840




















Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


References















10158401015840




















Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of










Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

research article distribution of picric acid into various...

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