4.1 Conformation Analysis of Alkanes
4.1 鐑风儍鐨勬瀯璞″垎鏋�
4.1.1 Conformation 4.1.1 鏋勮薄
At a molecular level, a property of 蟽 (sigma) bonds in alkane is that the bonds keep on rotating. For the example of ethane (CH3CH3), one methyl (CH3) group is able to rotate around the C-C bond freely without any obstacles.
鍦ㄥ垎瀛愭按骞充笂锛岀兎鐑冧腑 蟽 (sigma) 閿殑涓€涓壒鎬ф槸閿笉鏂棆杞€備互涔欑兎锛圕H 3 CH 3 锛変负渚嬶紝涓€涓敳鍩猴紙CH 3 锛夊彲浠ュ洿缁旵-C閿嚜鐢辨棆杞紝娌℃湁浠讳綍闅滅銆�
It is highly recommended that the molecular model is used here to 鈥渟ee鈥� the bond rotation. With a molecular model on hand, you can hold one methyl group steady, and rotate the other methyl group.
寮虹儓寤鸿鍦ㄨ繖閲屼娇鐢ㄥ垎瀛愭ā鍨嬫潵鈥滄煡鐪嬧€濋敭鏃嬭浆銆傛湁浜嗙幇鏈夌殑鍒嗗瓙妯″瀷锛屾偍鍙互绋冲畾鍦颁繚鎸佷竴涓敳鍩猴紝骞舵棆杞彟涓€涓敳鍩恒€�
The C-C bond is formed by the sp3-sp3 orbitals overlapping and the bond is cylindrically symmetrical, so rotation about the bond can occur easily and the molecule does not seem to change. However, a closer look indicates that the rotation of the C-C bond does result in a different spatial arrangement of hydrogen atoms in the molecule, as shown below:
C-C閿槸鐢眘p 3 -sp 3 杞ㄩ亾閲嶅彔褰㈡垚鐨勶紝璇ラ敭鏄渾鏌卞绉扮殑锛屽洜姝ゅ緢瀹规槗鍙戠敓缁曢敭鐨勬棆杞紝骞朵笖鍒嗗瓙浼间箮娌℃湁鍙樺寲銆傜劧鑰岋紝浠旂粏瑙傚療鍙戠幇锛孋-C閿殑鏃嬭浆纭疄瀵艰嚧浜嗗垎瀛愪腑姘㈠師瀛愮殑涓嶅悓绌洪棿鎺掑垪锛屽涓嬫墍绀猴細
Figure 4.1a Two conformers of ethane in perspective formulas
鍥� 4.1a 閫忚鍏紡涓箼鐑风殑涓や釜鏋勮薄寮傛瀯浣�
The different spatial arrangements of the atoms/groups that result from the single bond rotation are called conformations. Molecules with different conformations are called conformational isomers or conformers. The two extreme conformations of ethane coming from the C-C rotation shown above are: the staggered conformation with all of the H atoms spread out and the eclipsed conformation with all of the H atoms overlapped.
鐢卞崟閿棆杞骇鐢熺殑鍘熷瓙/鍩哄洟鐨勪笉鍚岀┖闂存帓鍒楃О涓烘瀯璞°€傚叿鏈変笉鍚屾瀯璞＄殑鍒嗗瓙绉颁负鏋勮薄寮傛瀯浣撴垨鏋勮薄寮傛瀯浣撱€備笂闈㈡樉绀虹殑鏉ヨ嚜 C-C 鏃嬭浆鐨勪箼鐑风殑涓ょ鏋佺鏋勮薄鏄細鎵€鏈� H 鍘熷瓙灞曞紑鐨勪氦閿欐瀯璞″拰鎵€鏈� H 鍘熷瓙閲嶅彔鐨勯噸鍙犳瀯璞°€�
In the study of conformation, it is convenient to use certain types of structural formulas. The formula used in the drawing above is the perspective formula (see section 2.1.1) that shows the side-view of the molecule. In perspective formulas, solid and dashed wedges are used to show the spatial arrangement of atoms (or groups) around the sp3 carbons.
鍦ㄦ瀯璞＄爺绌朵腑锛屼娇鐢ㄦ煇浜涚被鍨嬬殑缁撴瀯寮忔槸寰堟柟渚跨殑銆備笂鍥句腑浣跨敤鐨勫叕寮忔槸鏄剧ず鍒嗗瓙渚ц鍥剧殑閫忚鍏紡锛堝弬瑙佺2.1.1鑺傦級銆傚湪閫忚鍏紡涓紝瀹炵嚎鍜岃櫄绾挎褰㈢敤浜庢樉绀� sp 3 纰冲懆鍥村師瀛愶紙鎴栧熀鍥級鐨勭┖闂存帓鍒椼€�
Another structural formula is the sawhorse formula which shows the tilted top-view of the molecule.
鍙︿竴涓粨鏋勫紡鏄敮鏈ㄦ灦寮忥紝瀹冩樉绀轰簡鍒嗗瓙鐨勫€炬枩椤惰鍥俱€�
Figure 4.1b Two conformers of ethane in sawhorse formulas
鍥� 4.1b 閿湪鏋跺叕寮忎腑涔欑兎鐨勪袱绉嶆瀯璞″紓鏋勪綋
The most commonly applied formula in conformation analysis is the Newman projection formula.
鏋勮薄鍒嗘瀽涓渶甯哥敤鐨勫叕寮忔槸绾芥浖鎶曞奖鍏紡銆�
Figure 4.1c Two conformers of ethane in Newman projections
鍥� 4.1c 绾芥浖鎶曞奖涓箼鐑风殑涓や釜鏋勮薄寮傛瀯浣�
How to draw a Newman projection
濡備綍缁樺埗绾芥浖鎶曞奖
To draw a Newman projection, we will imagine viewing the molecule from one carbon to the next carbon atom directly along a selected C鈥�C bond, as shown below, and follow the rules:
涓轰簡缁樺埗绾芥浖鎶曞奖锛屾垜浠皢鎯宠薄鐩存帴娌跨潃閫夊畾鐨� C-C 閿粠涓€涓⒊鍘熷瓙鍒颁笅涓€涓⒊鍘熷瓙鐨勫垎瀛愶紝濡備笅鎵€绀猴紝骞堕伒寰鍒欙細
Figure 4.1d Viewing of the molecule
鍥� 4.1d 鍒嗗瓙瑙嗗浘
The front carbon atom is shown as a point with three other bonds:
鍓嶉潰鐨勭⒊鍘熷瓙鏄剧ず涓哄甫鏈夊叾浠栦笁涓敭鐨勭偣锛�
The rear carbon atom is shown as a circle with three other bonds:
鍚庨潰鐨勭⒊鍘熷瓙鏄剧ず涓哄甫鏈夊叾浠栦笁涓敭鐨勫渾鍦堬細
Put the two carbons together to get the Newman projection of the staggered conformation:
灏嗕袱涓⒊鏀惧湪涓€璧峰嵆鍙緱鍒颁氦閿欐瀯璞＄殑绾芥浖鎶曞奖锛�
From the staggered conformation, fix the front carbon in place and rotate the rear carbon by 60掳 to get the eclipsed conformation:
浠庝氦閿欐瀯璞′腑锛屽皢鍓嶇⒊鍥哄畾鍒颁綅锛屽苟灏嗗悗纰虫棆杞� 60掳锛屽緱鍒伴噸鍙犳瀯璞★細
Note: In eclipsed conformers, the C-H bonds are supposed to be completely overlapped; however, to make the rear groups still visible, the bonds on the rear carbon are intentionally drawn slightly tilted.
娉ㄦ剰锛氬湪閲嶅彔鏋勮薄寮傛瀯浣撲腑锛孋-H 閿簲璇ュ畬鍏ㄩ噸鍙狅紱鐒惰€岋紝涓轰簡浣垮悗鍩哄洟浠嶇劧鍙锛屽悗纰充笂鐨勯敭鏁呮剰绋嶅井鍊炬枩銆�
4.1.2 Conformation Analysis of Ethane
4.1.2 涔欑兎鐨勬瀯璞″垎鏋�
Next, we will do a conformation analysis of ethane by using the Newman projections. A conformation analysis is an investigation of the energy differences and relative stabilities of the different conformations of a compound.
鎺ヤ笅鏉ワ紝鎴戜滑灏嗕娇鐢ㄧ航鏇兼姇褰卞涔欑兎杩涜鏋勮薄鍒嗘瀽銆傛瀯璞″垎鏋愭槸瀵瑰寲鍚堢墿涓嶅悓鏋勮薄鐨勮兘閲忓樊寮傚拰鐩稿绋冲畾鎬х殑鐮旂┒銆�
The two conformations of ethane, staggered and eclipsed, are different and therefore should be in different energy levels. You may also intuitively predict that the staggered conformation is more stable and is lower energy because the C-H bonds are arranged as far apart as possible in that conformation. That is correct! In eclipsed conformations, the H atoms on the front carbon are overlapping with the H atoms on the rear carbon, and this arrangement causes the repulsion between the electrons of C-H bonds of the two carbons. This type of repulsion is called torsional strain, also known as eclipsing strain. Due to torsional strain, the eclipsed conformer is in an energy level that is 12 kJ/mol (or about 2.9 kcal/mol) higher than the staggered one. This can be represented graphically in a potential energy diagram as shown in Figure 4.1f.
涔欑兎鐨勪袱绉嶆瀯璞★紝浜ら敊鏋勮薄鍜岄噸鍙犳瀯璞℃槸涓嶅悓鐨勶紝鍥犳搴旇澶勪簬涓嶅悓鐨勮兘绾с€傛偍杩樺彲浠ョ洿瑙傚湴棰勬祴浜ら敊鏋勮薄鏇寸ǔ瀹氬苟涓旇兘閲忔洿浣庯紝鍥犱负鍦ㄨ鏋勮薄涓� C-H 閿帓鍒楀緱灏藉彲鑳借繙銆傞偅鏄鐨勶紒鍦ㄩ噸鍙犳瀯璞′腑锛屽墠纰充笂鐨凥鍘熷瓙涓庡悗纰充笂鐨凥鍘熷瓙閲嶅彔锛岃繖绉嶆帓鍒楀鑷翠袱涓⒊鐨凜-H閿數瀛愪箣闂寸殑鎺掓枼銆傝繖绉嶇被鍨嬬殑鎺掓枼绉颁负鎵浆搴斿彉锛屼篃绉颁负椋熷簲鍙樸€傜敱浜庢壄杞簲鍙橈紝閲嶅彔鏋勮薄寮傛瀯浣撶殑鑳界骇姣斾氦閿欐瀯璞″紓鏋勪綋楂� 12 kJ/mol锛堟垨绾� 2.9 kcal/mol锛夈€傝繖鍙互鐢ㄥ娍鑳藉浘鏉ヨ〃绀猴紝濡傚浘 4.1f 鎵€绀恒€�
Figure 4.1e Staggered vs. eclipsed conformation
鍥� 4.1e 浜ら敊鏋勮薄涓庨噸鍙犳瀯璞�
Fig. 4.1f Potential Energy 聽of Ethane vs the Angle of Rotation about the C-C bond
鍥� 4.1f 涔欑兎鍔胯兘涓� C-C 閿棆杞搴︾殑鍏崇郴
Because of this energy difference, an energy barrier must be overcome when rotation about the C-C bond occurs. However, this energy difference in ethane is small, and the kinetic energy of molecules at room temperature is high enough to cover it. So, at room temperature, the changes from staggered to eclipsed conformers occur millions of times per second. Because of these continuous interconversions, these two conformers cannot be separated from each other. However, at any given moment, about 99% of the ethane molecules will be in a staggered conformation because of their higher stability.
鐢变簬杩欑鑳介噺宸紓锛屽綋鍙戠敓鍥寸粫 C-C 閿殑鏃嬭浆鏃讹紝蹇呴』鍏嬫湇鑳介噺鍔垮瀿銆傜劧鑰岋紝涔欑兎涓殑杩欑鑳介噺宸緢灏忥紝骞朵笖瀹ゆ俯涓嬪垎瀛愮殑鍔ㄨ兘瓒冲楂樻潵瑕嗙洊瀹冦€傚洜姝わ紝鍦ㄥ娓╀笅锛屼粠浜ら敊鏋勮薄寮傛瀯浣撳埌閲嶅彔鏋勮薄寮傛瀯浣撶殑鍙樺寲姣忕鍙戠敓鏁扮櫨涓囨銆傜敱浜庤繖浜涜繛缁殑鐩镐簰杞寲锛岃繖涓や釜鏋勮薄寮傛瀯浣撲笉鑳藉郊姝ゅ垎绂汇€傜劧鑰岋紝鍦ㄤ换浣曠粰瀹氭椂鍒伙紝澶х害 99% 鐨勪箼鐑峰垎瀛愬皢澶勪簬浜ら敊鏋勮薄锛屽洜涓哄畠浠叿鏈夋洿楂樼殑绋冲畾鎬с€�
4.1.3 Conformation Analysis of Propane
4.1.3 涓欑兎鐨勬瀯璞″垎鏋�
A similar analysis can be applied to propane as well. There are still two types of conformations: staggered and eclipsed resulting from the rotation. The difference between propane and ethane is that there is a methyl (CH3) group connected on the rear carbon for propane. However, that does not affect the relative stability, and the staggered conformer is more stable and lower energy.
绫讳技鐨勫垎鏋愪篃閫傜敤浜庝笝鐑枫€備粛鐒舵湁涓ょ绫诲瀷鐨勬瀯璞★細浜ら敊鏋勮薄鍜屽洜鏃嬭浆鑰屼骇鐢熺殑閲嶅彔鏋勮薄銆備笝鐑峰拰涔欑兎鐨勫尯鍒湪浜庝笝鐑风殑鍚庣⒊涓婅繛鎺ユ湁鐢插熀锛圕H 3 锛夊熀鍥€€備絾杩欏苟涓嶅奖鍝嶇浉瀵圭ǔ瀹氭€э紝浜ら敊鏋勮薄寮傛瀯浣撴洿绋冲畾锛岃兘閲忔洿浣庛€�
Figure 4.1g Staggered and eclipsed conformation of propane
鍥� 4.1g 涓欑兎鐨勪氦閿欏拰閲嶅彔鏋勮薄
4.1.4 Conformation Analysis of Butane
4.1.4 涓佺兎鐨勬瀯璞″垎鏋�
There are three C-C bonds in butane, and rotation can occur about each of them. If we choose C1-C2 (or C3-C4) for the study, the situation is almost the same as propane, with the ethyl CH2CH3 group replacing the CH3 group. However, if we consider the rotation about the C2-C3 bond, the situation will be much more complex.
涓佺兎涓湁涓変釜 C-C 閿紝姣忎釜閿兘鍙互鍙戠敓鏃嬭浆銆傚鏋滄垜浠€夋嫨C1-C2锛堟垨C3-C4锛夎繘琛岀爺绌讹紝鎯呭喌鍑犱箮涓庝笝鐑风浉鍚岋紝鐢ㄤ箼鍩篊H 2 CH 3 鍩哄洟浠ｆ浛CH 3 缁勩€傜劧鑰岋紝濡傛灉鎴戜滑鑰冭檻C2-C3閿殑鏃嬭浆锛屾儏鍐靛氨浼氬鏉傚緱澶氥€�
Figure 4.1h Conformation analysis of butane by viewing along C2-C3 bond
鍥�4.1h 娌緾2-C3閿瀵熶竵鐑风殑鏋勮薄鍒嗘瀽
For both carbon atoms, C2 and C3, there are two hydrogen atoms and one methyl CH3 group bonded. We can start with the conformer in which the two CH3 groups are opposite to each other, then fix the front carbon and do 60掳 rotations of the rear carbon to investigate all the possible conformations.
瀵逛簬涓や釜纰冲師瀛愶紙C2 鍜� C3锛夛紝鏈変袱涓阿鍘熷瓙鍜屼竴涓敭鍚堢殑鐢插熀 CH 3 鍩哄洟銆傛垜浠彲浠ヤ粠涓や釜CH 3 鍩哄洟鐩稿鐨勬瀯璞″紑濮嬶紝鐒跺悗鍥哄畾鍓嶉潰鐨勭⒊锛屽皢鍚庨潰鐨勭⒊鏃嬭浆60掳鏉ョ爺绌舵墍鏈夊彲鑳界殑鏋勮薄銆�
Exercises 4.1: Draw all the possible conformers of butane from viewing along the C2-C3 bond. Finish this practice by yourself before continue reading!
缁冧範 4.1锛氭部鐫€ C2-C3 閿瀵燂紝鐢诲嚭涓佺兎鎵€鏈夊彲鑳界殑鏋勮薄寮傛瀯浣撱€傚湪缁х画闃呰涔嬪墠锛岃鑷瀹屾垚姝ょ粌涔狅紒
Tips for drawing all the possible conformers about a certain C-C bond:
缁樺埗鏌愪釜 C-C 閿殑鎵€鏈夊彲鑳芥瀯璞″紓鏋勪綋鐨勬妧宸э細
View along that C-C bond; circle and decide what atoms/groups are connected on each carbon;
娌跨潃 C-C 閿煡鐪嬶紱鍦堝嚭骞剁‘瀹氭瘡涓⒊涓婅繛鎺ョ殑鍘熷瓙/鍩哄洟锛�Start with the staggered conformation in which the largest groups on each carbon are opposite (far away) to each other (this is called the 鈥�anti鈥�conformation as we will learn later);
浠庝氦閿欐瀯璞″紑濮嬶紝鍏朵腑姣忎釜纰充笂鏈€澶х殑鍩哄洟褰兼鐩稿锛堣繙锛夛紙杩欑О涓衡€滃弽鈥濇瀯璞★紝鎴戜滑绋嶅悗灏嗕簡瑙ｅ埌锛夛紱Keep the groups on one carbon 鈥渇ixed鈥�, and rotate the groups on the other carbon at 60掳 angles. Repeat the rotation five times, and you should get total of six conformers.
淇濇寔涓€涓⒊涓婄殑鍩哄洟鈥滃浐瀹氣€濓紝骞朵互 60掳 瑙掓棆杞彟涓€涓⒊涓婄殑鍩哄洟銆傞噸澶嶆棆杞簲娆★紝浣犲簲璇ュ緱鍒版€诲叡鍏釜鏋勮薄寮傛瀯浣撱€�
Answers to Chapter 4 Practice Questions绗� 4 绔犵粌涔犻绛旀
Figure 4.1i All the conformers of butane by viewing along C2-C3 bond
鍥�4.1i 娌緾2-C3閿瀵熶竵鐑风殑鎵€鏈夋瀯璞″紓鏋勪綋
Among all six conformers obtained, there are three staggered and three eclipsed. Staggered conformations C and E should be in the same energy level because the groups are arranged in an equivalent way between these two conformers. Similarly, eclipsed conformations F and B are also in the same energy level. So, our studies can be focused on the four conformers: A, B, C and D, which are different in terms of energy and stability.
鍦ㄨ幏寰楃殑鎵€鏈夊叚涓瀯璞″紓鏋勪綋涓紝鏈変笁涓氦閿欏紓鏋勪綋鍜屼笁涓噸鍙犳瀯璞″紓鏋勪綋銆備氦閿欐瀯璞� C 鍜� E 搴旇澶勪簬鐩稿悓鐨勮兘绾э紝鍥犱负杩欎袱涓瀯璞′綋涔嬮棿鐨勫熀鍥互绛夋晥鏂瑰紡鎺掑垪銆傚悓鏍凤紝閲嶅彔鏋勮薄F鍜孊涔熷浜庣浉鍚岀殑鑳界骇銆傚洜姝わ紝鎴戜滑鐨勭爺绌跺彲浠ラ泦涓湪鍥涚鏋勮薄寮傛瀯浣擄細A銆丅銆丆鍜孌锛屽畠浠湪鑳介噺鍜岀ǔ瀹氭€ф柟闈㈡湁鎵€涓嶅悓銆�
Between the two staggered conformers A and C, A is more stable than C because the two methyl CH3 groups in A are as far apart as possible. This most stable staggered conformation is called the anti鈥�conformation (anti is Greek for 鈥渙pposite鈥�). In anti鈥�conformations, the largest groups on the front and rear carbon are 180掳 opposite to each other. The other staggered conformation C is called a gauche conformation, in which the two large groups are adjacent and are 60掳 to each other. With the large groups being close to each other in gauche conformers, the molecule experiences steric strain. Steric strain is the strain that is caused when atoms (or groups) are close enough together that their electron clouds repel each other. Steric strain only matters when the groups are close to each other (less or equal to 60掳), so steric strain does not apply in anti-conformations. The magnitude of steric strain also depends on the size of the group: the larger the size, the higher the steric strain. As a result, there is no steric strain between two small hydrogen atoms, even if they are close to each other.
鍦ㄤ袱涓氦閿欐瀯璞″紓鏋勪綋A鍜孋涔嬮棿锛孉姣擟鏇寸ǔ瀹氾紝鍥犱负A涓殑涓や釜鐢插熀CH3鍩哄洟璺濈灏藉彲鑳借繙銆傝繖绉嶆渶绋冲畾鐨勪氦閿欐瀯璞＄О涓哄弽鏋勮薄锛坅nti 鏄笇鑵婅锛屾剰涓衡€滅浉鍙嶁€濓級銆傚湪鍙嶆瀯璞′腑锛屽墠鍚庣⒊涓婃渶澶х殑鍩哄洟褰兼鎴�180掳鐩稿銆傚彟涓€绉嶄氦閿欐瀯璞绉颁负gauche鏋勮薄锛屽叾涓袱涓ぇ鍩哄洟鐩搁偦涓斿郊姝ゆ垚60掳銆傜敱浜庡ぇ鍩哄洟鍦ㄧ矖淇楁瀯璞′綋涓郊姝ら潬杩戯紝鍒嗗瓙浼氱粡鍘嗙┖闂村簲鍙樸€備綅闃诲簲鍙樻槸褰撳師瀛愶紙鎴栧熀鍥級瓒冲鎺ヨ繎浠ヨ嚦浜庡畠浠殑鐢靛瓙浜戠浉浜掓帓鏂ユ椂寮曡捣鐨勫簲鍙樸€傜┖闂村簲鍙樹粎鍦ㄥ熀鍥㈠郊姝ゆ帴杩戯紙灏忎簬鎴栫瓑浜� 60掳锛夋椂鎵嶉噸瑕侊紝鍥犳绌洪棿搴斿彉涓嶉€傜敤浜庡弽鏋勮薄銆傜┖闂村簲鍙樼殑澶у皬杩樺彇鍐充簬鍩哄洟鐨勫ぇ灏忥細灏哄瓒婂ぇ锛岀┖闂村簲鍙樿秺楂樸€傚洜姝わ紝鍗充娇涓や釜灏忔阿鍘熷瓙褰兼闈犺繎锛屽畠浠箣闂翠篃涓嶅瓨鍦ㄧ┖闂村簲鍙樸€�
Figure 4.1j Anti and gauche conformations
鍥�4.1j Anti鍜実auche鏋勮薄
Between the two eclipsed conformers B and D, D is less stable than B because the two CH3 groups are eclipsing (overlapping) each other in D, causing both torsional and steric strains.
鍦ㄤ袱涓噸鍙犳瀯璞″紓鏋勪綋 B 鍜� D 涔嬮棿锛孌 姣� B 鏇翠笉绋冲畾锛屽洜涓轰袱涓� CH 3 鍩哄洟鍦� D 涓郊姝ら噸鍙狅紙閲嶅彔锛夛紝浠庤€屽鑷存壄杞拰绌洪棿搴斿彉銆�
Figure 4.1k Comparison between the two eclipsed conformations
鍥�4.1k 涓ょ閲嶅彔鏋勮薄鐨勬瘮杈�
The energy difference of all the conformers obtained from the rotation about the C2-C3 bond are shown in the potential energy diagram Fig. 4.1l. The curve is more complex than that of ethane since there are four different energy levels corresponding to four conformers with different stabilities. Even the energy barriers for the rotations are larger than that of ethane, but they are still not high enough to stop rotation at room temperature.
缁旵2-C3閿棆杞緱鍒扮殑鎵€鏈夋瀯璞″紓鏋勪綋鐨勮兘閲忓樊濡傚浘4.1l鍔胯兘鍥炬墍绀恒€傝鏇茬嚎姣斾箼鐑风殑鏇茬嚎鏇村鏉傦紝鍥犱负鏈夊洓绉嶄笉鍚岀殑鑳界骇瀵瑰簲浜庡叿鏈変笉鍚岀ǔ瀹氭€х殑鍥涚鏋勮薄寮傛瀯浣撱€傚嵆浣挎棆杞殑鑳藉瀿姣斾箼鐑峰ぇ锛屼絾瀹冧滑浠嶇劧涓嶈冻浠ュ湪瀹ゆ俯涓嬪仠姝㈡棆杞€�
Figure 4.1l Potential Energy of Butane vs the Angle of Rotation about the C2-C3 bond
鍥� 4.1l 涓佺兎鍔胯兘涓� C2-C3 閿棆杞搴︾殑鍏崇郴
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